Category: 36805-97-7

Application of 36805-97-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Tert-butyl 2-acetyl-3 – ((tert-butyldimethylsilyl) oxy) -5- (methoxymethyloxy) -6- (pivaloyloxy) benzoate (5.00 g, 9.79 mmol, 1 eq) 0 g), and the temperature was raised to 85 C. Subsequently, N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added thereto, followed by stirring at 85 C. After stirring for 2.5 hours, it was cooled to room temperature and concentrated under reduced pressure to remove half of the solvent amount (25.0 g). The same amount of toluene as the distilled solvent was added and heated again to 85 C. Then N, N-dimethylformamide-di-tert-butylacetal (1.99 g, 9.79 mmol, 1 eq) was added and the mixture was incubated for 2 hours did. The reaction solution was concentrated under reduced pressure until the solvent disappeared, toluene was added to this concentrated solution, the total amount was adjusted to be 20 times by weight of the product on the assumption that the yield was 100%. Iodine (2.02 g, 7.96 mmol, 3 eq) and pyridine (0.21 g, 2.65 mmol, 1 eq) were added to 30.0 g of the adjusted solution (estimated to contain 1.50 g of enamine compound, 2.65 mmol) C. for 2 hours. Acetic acid (0.30 mL, 5.30 mmol, 2 eq) was added after confirming the disappearance of the raw material by HPLC analysis, and after reacting at 50 C. for 3 hours and 30 minutes, 15% aqueous sodium thiosulfate solution (26.7 g) Was added and stirred, and the organic phase was taken out. The organic phase was washed with water (7.5 g) and concentrated under reduced pressure. Toluene was added to the obtained crude product, and the total amount was adjusted to 5.2 g. Heptane (7.0 g) was added to the solution, and the mixture was cooled to 5 C. and recrystallized to obtain tert-butyl 3-iodo-7- (methoxymethyloxy) -4-oxo-6- (pivaloyloxy) -4H- Chromene-5-carboxylate as a white solid (yield 72.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; Tanaka, Yui; Fujiwara, Yuji; (25 pag.)JP2015/113324; (2015); A;,
Ether – Wikipedia,
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Synthetic Route of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation GW-(2,6-diethylphenyl)-5-[(2E)-3-(dimethyta [(VI) R2 =Me, R3 = CONHR”, R” = 2,6-diethylphenyl]step 5To a solution of 5-acetyl-/V-(2,6-diethylphenyl)-1-methyl-1 H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), A/,A/-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80C for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2S04, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017g, 78% yield).1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1 H), 7.71 (d, J =12.33 Hz, 1 H), 7.36 (s, 1 H), 7.21 (t, J =7.60 Hz, 1 H), 7.12 (d, J =7.60 Hz, 2 H), 5.75 (d, J =12.33 Hz, 1 H), 4.18 (s, 3 H), 3.16 (s, 3 H), 2.92 (s, 3 H), 2.52 (q, J =7.57 Hz, 4 H), 1.09 (t, J =7.57 Hz, 6 H)HRMS (ESI) calcd for C20H27N4O2 [M +H]+ 355.2129, found 355.2133.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; CASUSCELLI, Francesco; BRASCA, Maria Gabriella; CALDARELLI, Marina; CERVI, Giovanni; DISINGRINI, Teresa; QUARTIERI, Francesca; WO2012/139930; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2,6-Dichloro-isonicotinic acid (11.2 g, 57.1 mmol) is suspended in toluene (150 mL) at 800C and then treated with N,N-dimethylformamide di-tert.-butyl acetal (50 mL, 209 mmol).The dark mixture is stirred at 800C for 12 h, then at rt for 16 h. The dark solution is diluted with diethyl ether (400 mL), washed with sat. aq. NaHCO3 solution (3×100 mL), dried overNa2SO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:ethyl acetate to give 2,6-dichloro-isonicotinic acid tert. -butyl ester (14.2 g) as a brownish oil which slowly solidifies; LC-MS: tR = 1.05 min; 1H NMR (D6-DMSO): £1.56 (s, 9 H), 7.85 (s, 2 H).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

To a solution of 2,6-dichloroisonicotinic acid (2 g, 10.4 mmol) in toluene (50 mL) N,N dimethylformamide di-tert-butil acetal (15 mL, 62.5 mmol) was added under nitrogen atmosphere and mixture heated at 80 Ethyl acetate was added and organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated to yield the title compound (2.34 g, 87%) as a solid.LRMS (m/z): 249 (M+1)+.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.60 (s, 9 H) 7.74 (s, 2 H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 36805-97-7.

Related Products of 36805-97-7, A common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A suspension of 4-bromo-3-methylbenzoic acid (10 g, 46.5 mmol) was heated to 80 C. and N,N-dimethylformamide di-tert-butyl acetal (44.6 mL, 186.0 mmol) was added dropwise over 30 minutes under a nitrogen atmosphere; stirring was continued at this temperature for 1.5 h. The reaction mixture was allowed to cool and then washed with water (1*), saturated NaHCO3 (1*), and brine (1*). The organic layer was dried (Na2SO4) and concentrated to afford tert-Butyl 4-bromo-3-methylbenzoate (as an off-white oil (8.8 g, 70%). ESI-MS m/e 311.9 (M+CH3CN+1).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference of 36805-97-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36805-97-7 as follows.

1 ,1-Di-tert-butoxy-W,A/-dimethylmethanamine (1.03 ml, 4.30 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1 -ethyl-1 H-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 39 (380 mg, 1.08 mmol) in toluene (10 ml). The reaction was heated at 80 C for 2 h then allowed to cool to RT. 1 ,1-Di-tert-butoxy-A/,/v- dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 80 C for 3 h then allowed to cool to RT. 1 ,1-Di-terf-butoxy-A/,W-dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 110 C for 1 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (20 ml) then washed with water (2 x 20 ml), saturated aq. NaHC03 solution (2 x 20 ml) and brine (10 ml), then dried over Na2S04, filtered and evaporated to afford an orange solid (510 mg). The crude material was purified by flash column chromatography on a silica column (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 0:100 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a white solid (320 mg, 72%).1H NMR (500 MHz, DMSO-de) delta 8.07 (s, 1 H), 7.98 (t, J = 5.8 Hz, 1 H), 7.77 (dd, J = 8.4, 1.3 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.41 – 7.12 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 5.9 Hz, 2H), 4.38 – 4.24 (m, 2H), 1.58 (s, 9H), 1.29 (t, J = 7.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 4 0 [MH+], R, = 1.17 min, UV purity = 99%.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C11H25NO2

Step (2): synthesis of 4-formyl-benzoic acid tert-butyl ester:; 4-Formylbenzoic acid was suspended in 60 mL of benzene, and the mixture was placed under a nitrogen atmosphere. The mixture was brought to reflux and N,N -dimethylformamide di-tert-butylacetal was added dropwise via an addition funnel over 45 minutes. The yellowish suspension gradually turned golden yellow and became a homogeneous solution. The solution was refluxed an additional 60 minutes before stirring overnight at room temperature. The resulting orange solution was diluted to about 100 mL with ethyl acetate (“EtOAc”), and the resulting solution was washed sequentially with water, saturated sodium bicarbonate (2 x 100 mL), and brine (100 mL). The solvent was removed by rotary evaporation. The resulting amber oil was injected on to a BIOTAGE Flash 65i (350 g, silica gel) cartridge and purified with a 30-minute gradient of from 5% to 25% v/v EtOAc in heptane. Product fractions were pooled, and the solvent was rotary evaporated. The resulting golden oil was dried under house high vacuum overnight at room temperature to give 3.92 g (57% yield) of 4- formyl-benzoic acid tert-butyl ester as a yellow solid; IH NMR (400 MHz, DMSO-D6) delta ppm 1.54 (s, 9 H) 8.00 (dm, /=8.30, Hz, 2 H) 8.07 (dm, /=8.30, 2 H) 10.08 (s, 1 H); Mass Spectrum MH” 206.

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/61715; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C11H25NO2

C. 3-[5-(3,4-Dichloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazol-3-yl]-propionic acid tert-butyl ester. To a 3-neck round bottom flask fitted with an air condenser was added 3-[5-(3,4-dichloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazol-3-yl]-propionic acid (1.0 g, 2.3 mmol, 1.0 equiv) and toluene (23 mL) under nitrogen. The mixture was heated to 80 C. then N,N-dimethyl-di-tert-butylacetal (2.36 g, 11.6 mmol, 5.0 equiv) was added dropwise (neat). The reaction mixture was heated at 80 C. for 1 h then additional N,N-dimethyl-di-tert-butylacetal (2.36 g, 11.6 mmol, 5.0 equiv) was added. This mixture was stirred at 80 C. for 2 h then cooled to room temperature and partitioned between water (100 mL) and ether (100 mL). The organic layer was washed with 1 M sodium hydroxide (50 mL), water (50 mL) then brine (50 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude material was then purified by flash chromatography (20% ethyl acetate/hexanes) to afford the desired ester (1.1 g, >99%). HPLC: Rt=3.59 (Method A). MS (ESI): mass calculated for C22H20Cl4N2O2, 484.03; m/z found, 485.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.81 (d, J=2.2 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H), 7.61-7.59 (m, 2H), 7.48 (d, J=2.2 Hz, 1H), 7.05 (dd, J=8.2, 1.9 Hz, 1H), 6.71 (s, 1H), 2.87 (t, J=7.4 Hz, 2H), 2.61 (t, J=7.4 Hz, 2H), 1.38 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36805-97-7, its application will become more common.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 36805-97-7, The chemical industry reduces the impact on the environment during synthesis 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, I believe this compound will play a more active role in future production and life.

To a hot (80 C)solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250mL), N,N-dimethylformamide di-tert-butylacetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 80 C for 8 hand at rt for 16 h before another portion of N,N-dimethylformamidedi-tert-butyl acetal (5.67 g, 25.1mmol) was added. Stirring was continued at 80 C for 16 h. The mixture wascooled to rt, diluted with EtOAc and washed with sat. aq. NaHCO3-solutionfollowed by water. The org. layer was separated, dried over Na2SO4,filtered, evaporated and dried under high vacuum at 40 C to give tert-butyl 4-bromo-3-methyl benzoate(2.31 g, 61%) as a pale yellow oil; LC-MS: tR = 1.10 min, [M+1]+ = not detectable. 1HNMR (CDCl3): d 7.86(s, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.59 (d, J = 8.3 Hz, 1 H),2.46 (s, 3 H), 1.61 (s, 9 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lescop, Cyrille; Mueller, Claus; Mathys, Boris; Birker, Magdalena; De Kanter, Ruben; Kohl, Christopher; Hess, Patrick; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Steiner, Beat; Weller, Thomas; Bolli, Martin H.; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 222 – 238;,
Ether – Wikipedia,
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