Category: 89521-55-1

Adding a certain compound to certain chemical reactions, such as: 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 89521-55-1, Recommanded Product: 89521-55-1

107C. 3:1 regio isomeric mixture of tert-butyl 4-(2-amino-3- (benzyloxy)phenylcarbamo vD- 1 -( 1 H-pyrazo Io [3 ,4-d1pyrimidin-4- yl)piperidin-4- ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l-(lH- pyrazolor3,4-dlpyrimidin-4-yl)piperidin-4-ylcarbamate.N,N-Diisopropylethylamine (6.58 mL, 37.75 mmol) was added in one portion to a stirred suspension o f 4-(tert-butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidine-4-carboxylic acid (9.12 g, 25.17 mmol) and O-(7-Azabenzotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (10.53 g, 27.68 mmol) in NMP (60 mL). The mixture was warmed to 5O0C for 15 minutes under nitrogen and cooled to 2O0C. 3-(benzyloxy)benzene-l,2-diamine (5.39 g, 25.17 mmol) was added in one portion and the resulting solution was stirred at 20 0C for 70 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (3 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product which was purified by flash silica chromatography, elution gradient 1 to 10% MeOH in DCM. Fractions containing product were were evaporated to dryness to afford a pink foam which was shown to be an 82% pure 3:1 regio isomeric mixture of tert- butyl 4-(2-amino-3 -(benzyloxy)phenylcarbamoyl)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4- yl)piperidin-4-ylcarbamate and tert-butyl 4-(2-amino-6-(benzyloxy)phenylcarbamoyl)-l- (lH-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-ylcarbamate. (8.1g, 58% of 82% pure), m/z (ESI+) (M+H)+ = 559; HPLC tR = 2.21 min (28%), 2.41 min (72%); IH NMR (399.9 MHz, DMSO-d6) delta 1.44 (9H, d), 1.96 (0.5H, m), 2.13 (1.5H, s), 3.72 (2H, d), 4.31 (IH, m), 4.46 (IH, m), 4.94 (0.5H, s), 5.13 (1.5H, s), 6.28 (0.25H, d), 6.32 (0.25H, d), 6.51 (0.75H, t), 6.62 (0.75H, s), 6.81 (0.75H, d), 6.90 (0.25H, m), 7.22 – 7.43 (6H, m), 7.50 (1.5H, d), 8.15 (0.25H, s), 8.25 (IH, m), 8.32 (0.75H, s), 8.61 (0.25H, s), 9.10 (0.75H, s), 13.51 (IH, s)

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, 3-(Benzyloxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); A1;,
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Synthetic Route of 89521-55-1, 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 89521-55-1 as follows.

EXAMPLE 27; Ethyl[8-(benzyloxy)-3-oxo-3,4-dihydroquinoxaline-2(1H)-ylidene]acetate 60a; To 3-(benzyloxy)benzene-1,2-diamine (300 mg, 1.4 mmol) in solution in 2 ml of acetic acid, add diethyloxalacetate sodium salt (295 mg, 1.4 mmol) and stir under reflux for 2 hours. Evaporate to dryness and chromatograph to obtain the abovenamed product. Yield: 20%. 1H-NMR (200 MHz, DMSO-d6): delta 11.39 (broad s, 1H, NH), 8.70 (broad s, 1H, NH), 7.53-7.37 (m, 5H arom.), 6.93-6.84 (t, 1H, J=8 Hz, 1H arom.), 6.71-6.67 (d, 1H, J=8 Hz, 1H arom.), 6.57-6.53 (d, 1H, J=8 Hz, 1H arom.), 5.84 (s, 1H, CCH), 5.29 (s, 1H, OCH2-Ph), 4.30-4.20 (q, 2H, J=7 Hz, OCH2-CH3), 1.35-1.28 (t, 3H, J=7 Hz, OCH2CH3).

According to the analysis of related databases, 89521-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schmitt, Martine; Klotz, Evelyne; Macher, Jean-Paul; Bourguignon, Jean-Jacques; Abarghaz, Mustapha; Wagner, Patrick; Ronsin, Gael; US2006/183909; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 89521-55-1, 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 89521-55-1 as follows.

Example 1 Preparation of 4-benzyloxybenzimidazole STR109 A mixture of 3-benzyloxy-1,2-diaminobenzene 1.6 g (0.0073 mol) and formic acid (2.6 g, 0.057 mol) was heated to reflux for 1.5 h. The resulting mixture was then cooled, dissolved in methylene chloride, washed with 10% sodium carbonate solution, dried (Na2 SO4) and evaporated to dryness in vacuo. The residue was recrystallized from acetonitrile to give the title compound in 0.75 g (46%) yield, m.p. 165-167 C.

According to the analysis of related databases, 89521-55-1, the application of this compound in the production field has become more and more popular.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a stirred solution of 3- benzyloxybenzene-1,2 -diamine (1 g, 4.67 mmol) in AcOH (20 mL) was added with tetramethoxymethane (0.95 g, 7 mmol) in one portion at 20 oC. The solution was stirred overnight. Then the mixture was concentrated in vacuo. The residue was purified by prep-HPLC (neutral condition) to afford 4-benzyloxy-2- methoxy-1H- benzimidazole (0.7 g, 56%) as a white powder. LCMS (M+H+) m/z: Calcd: 255.11; Found: 255.1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Related Products of 89521-55-1, A common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, molecular formula is C13H14N2O, 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.

To a solution of Compound (6) (1.0 g), 3-(benzyloxy)-1,2-benzenediamine (817 mg) and 1-hydroxybenzotriazole (567 mg) in N,N-dimethylformamide (19 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (804 mg). After stirring for 6 hrs, saturated aqueous NaHCO3 (20 mL) and water (80 mL) were added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water. To a mixture of this product in acetic acid (7 mL) was added a solution of hydrogen chloride in acetic acid (13 mL). After stirring at 100 C. for 1 hour, the resulting mixture was cooled to 4 C. and diluted with ethyl acetate (40 mL). The resulting precipitate was collected by filtration and washed with ethyl acetate. To a solution of this product, O-tetrahydro-2H-pyran-2-ylhydroxylamine (1.5 eq.) and 1-hydroxybenzotriazole (1.5 eq.) in N,N-dimethylformamide (11 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.5 eq.) at 4 C. The mixture was warmed to ambient temperature and stirred for 8 hrs. The reaction mixture was added saturated NaHCO3 (11 mL) and water (44 mL). A resulting precipitate was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was treated with trifluoroacetic acid to give Compound E120 (52 mg). 1H-NMR (300 MHz, DMSO-d6, delta): 4.43 (2H, s), 6.46 (1H, d, J=16 Hz) 6.86 (1H, d, J=8 Hz), 7.12(1H, d, J=8 Hz), 7.23-7.30 (1H, m), 7.39-7.62 (5H, m);

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; US2004/229889; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 89521-55-1, These common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, 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.

To a stirred solution of 3-(benzyloxy)benzene-1,2-diamine 4g (4.67 mmol) in xylenes (10 mL), 2-(4-hydroxyphenyl) acetic acid (9.34 mmol) and boric acid (0.46 mmol) were added. The resulting solution was refluxed for 48 h. After cooling to room temperature, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by flash silica gel (230-400 mesh) column chromatography to afford the title compounds 6g. Yield 22%; White solid; mp 105-109 C; IR (neat) 3400-2600 (br., peak), 2921, 2850, 1594, 1515, 1442, 1245, 1172,1098, 1022, 837, 784, 732; 1H NMR (300 MHz, Methanol-d4) delta 7.46-7.57 (m, 2H), 7.26-7.40 (m, 3H), 7.06-7.14 (m,4H), 6.75-6.80 (m, 1H), 6.68-6.74 (m, 2H), 5.23 (s, 2H),4.08 (s, 2H); 13C NMR (100 MHz, Methanol-d4) delta 157.7,155.3, 149.1, 138.9, 131.0, 129.7, 129.4, 129.2, 129.1,124.1, 116.8, 116.7, 108.8, 105.7, 71.6, 35.2; HRMS (ESI) Calcd for C21H18N2O2 [M + H]+ 331.1446, found 331.1471.

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boggu, Pulla Reddy; Venkateswararao, Eeda; Manickam, Manoj; Kim, Youngsoo; Jung, Sang-Hun; Archives of Pharmacal Research; vol. 40; 4; (2017); p. 469 – 479;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem