Category: 131713-50-3

Reference of 131713-50-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[(3 S)-(7-BroMo-2-oxo-5-pyridin-2-yl-2, 3 -dihydro- 1H-benzo[e] [1,4] diazepin-3 -yl)-propionic acid Methyl ester (Compound of formula TV, S enantiomer,25.0 gr) and dichloromethane (?IVIDC?, 375 ml) were charged into a clean, dry 4 neck RBF. The reaction mixture was stirred for 5-10 minutes at temperature of 20-25C and a clear solution was obtained. 2-bromo pyridine (29.46 gr) was added to the solution and the obtained reaction mixture was stirred for 5-10 minutes. The obtained reaction mass was cooled down to a temperature of -15 to -20C. Then, Triflic anhydride (26.32 gr) was slowly added, over a period of 30-45 minutes to the cooled reaction mass, at the same temperature of-15 to -20C. After the addition was completed, the obtained reaction mixture was stirred for 30-45 minutes, at the same temperature of -15 to -20C. The reaction progress was monitored by HPLC (monitor intermediate (S)-3 -(2-(methoxycarbonyl)ethyl)-7-bromo-5 – (pyridin-2-yl)-3H-benzo [e] [1,4] diazepin-2-yl trifluoromethanesulfonate formation). Afterwards, 1-amino-2,2-dimethoxypropane (14.81 gr) in dichloromethane (2 vol, 50 mL) solution was slowly added over a period of about 30 minutes to the reaction mixture at temperature of -15 to -20C. After complete addition, Triethylamine (31.44 gr) was slowly added over a period of about 30 minutes at the same temperature of -15 to -20C, and the obtained mixture was stirred at temperature of -15 to -20C for 60-120 minutes. The reaction progress was monitored by HPLC. After the reaction was completed, ammonium chloride solution (20%, 125 ml) was added, and the temperature was raised to 15-20C; the obtained mixture was stirred for 30 minutes. The organic layer was separated, washed with DM water (125 ml) and re-separated. The organic layer was then concentrated to volume of 1-1.5 vol, at a temperature below 45C. Toluene (50m1) was added to the reaction mass, and then stripped out 1 vol under vacuum at a temperature below 60C. Then, Toluene (50m1) was added and the obtained mixture was heated to temperature of 60-65C, and was stirred at this temperature for 30-45 minutes. Heating was discontinued and the reaction mass was slowly cooled to temperature of 0-10C, and was stirred for 3-4 hours – crystallization occurred. The obtained suspension was stirred at temperature of 0-10C for 3 0-45 minutes. The obtained solid was filtered and washed twice with pre-cooled (temperature of about 5-10 C) toluene (12.5 ml X 2 times), and suck-dried for 20-30 minutes. The wet solid was further dried under vacuum at temperature of 40-45C for 6-8 hours. Yield (dry): 26.5 gm (85%)

The synthetic route of 2,2-Dimethoxypropan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON LABORATORIES INC.; BEN-ZION, Dolitzky; MARIOARA, Mendelovici; RAJARAM, Bodkhe Arjun; SHIVAJI, Mane Ganesh; SRIHARI, Samala Rajamouli; VIJAY, Joshi Ashutosh; LUTHRA, Parven Kumar; SINGH, Amit; MUTHUSAMY, Anantha Rajmohan; (62 pag.)WO2018/148361; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine, A new synthetic method of this compound is introduced below., SDS of cas: 131713-50-3

Step 1 A solution of Cbz-D-Valine (500 g, 1.99 mol) and N-methylmorpholine (201.8 g, 1.99 mol) in anhydrous THF (8 L) was cooled to -15 C., i-butylchlorofomate (299 g, 2.19 mol) was added dropwise under stirring. After 30 min, a solution of 1-amino-2,2-dimethoxypropane (209.5 g, 1.99 mol) in THF (1 L) was added slowly and the temperature was maintained at -15 C. for 2 h. The reaction mixture was washed with brine (2 L) and the organic phase was concentrated to remove the THF. The residue was diluted with EtOAc (4 L), washed with 1N aqueous HCl (2*2 L), washed with sat. NaHCO3 (2 L) and Na2CO3 (2 L), and washed with brine (1.5 L). After drying over Na2SO4, the organic solvent was removed under reduce pressure to afford (R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate as a white solid (670 g, yield 99.5%), which was used for next step without further purification. LC-MS m/z 360.9 [M+Na]+. 1H NMR (CD3OD 300 MHz): delta 7.35-7.30 (m, 5H), 5.08 (s, 2H), 4.45-4.35 (m, 1H), 3.95-3.85 (m, 1H), 3.34-3.25 (m, 8H), 2.10-1.90 (m, 1H), 0.94-0.91 (m, 6H).

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.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 131713-50-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The precursor 2,2-dimethoxypropylamine can be preparedaccording to the methodology described, for example, in Cui, P.et al., Bioorganic & Medicinal Chemistry Letters, 2006, 16(13),3401-3405. A previously prepared solution of 2,2- dimethoxypropylamine in anhydrous tetrahydrofuran (5.4 g of the amine (41.16 mmol) in 50 mL of the organic solvent) was slowlyadded at a temperature of -5C to the solution obtained according to the methodology described in Comparative Example 6. Once the addition ended, the temperature of the obtained mixture was increased to about 20C, and it was kept under stirring for 16 hours at a temperature of about 20C.Once it no longer had to be kept under the aforementioned conditions, 50 mL of an 8% aqueous NaHCO3 solution and 50 mL of 2-methyltetrahydrofuran were added. The resulting mixture was kept under stirring for about 5 minutes and the resulting organic phase containing (3S)-3-[7-bromo-2-(2,2-dimethoxypropylamino)-5-pyridin-2-yl-3H-benzo[e] [l,4]diazepin-3- yl]propionic acid methyl ester was subsequently separated. The organic solvent was vacuum-distilled, and 50 mL of acetone were added to the resulting residue. The obtained mixture was heated at the reflux temperature and then slowly cooled to about 20C.The resulting solid was filtered and oven-dried, finally obtaining 5.2 g (75.7% from 3-[(3S)-7-bromo-2-oxo-5-(pyridin-2- yl)-2,3-dihydro-1H-[1,4]-benzodiazepin-3-yl] propionic acid methyl ester of formula (D), with a purity of 98.5% by means of UPLC) of (3S)-3-[7-bromo-2-(2,2-dimethoxypropylamino)-5-pyridin- 2-yl-3H-benzo[e] [1,4]diazepin-3-yl]propionic acid methyl ester.Figure 6 shows the 1H-NMR spectrum. 1H-NMR (CDC13, 400 MHz)6 (ppm) : 8.65 (1H, d) , 7.79 (2H, m) , 7.48 (1H, dd) , 7.35 (2H, m)7.10 (1H, d) , 5.18 (1H, m) , 3.70 (3H, s) , 3.64 (1H, dd) , 3.45(1H, dd), 3.31 (1H, dd), 3.22 (3H, s), 3.21 (3H, s), 2.77(1H,m) , 2.65-2.37 (3H, m) , 1.72 (1H, s) , 1.29 (3H, s)Figure 7 shows the 13C-NMR spectrum. 13C-NMR (CDC13, 400MHz) 6(ppm): 173.31, 167.89, 156.77, 154.75, 149.57, 149.16,136.57, 133.78, 133.07, 128.51, 127.10, 124.44, 124.24, 112.33,100.14, 60.24, 51.80, 48.65, 48.62, 45.72, 30.84, 26.23, 20.57.

The synthetic route of 2,2-Dimethoxypropan-1-amine has been constantly updated, and we look forward to future research findings.