3-Amino-2,2-dimethylpropanamide

White Solid

A mixture of 2-cyano-2-methylpropanamide (40 g, 0.357 mol), Raney.(R). nickel (8 g), a 10percent solution of ammonia in methanol (63.75 mL, 0.375 mol) and methanol (320 mL) were placed in autoclave system at 25-35°C and stirred for 5- 10 min. The resulting reaction mixture was heated to 60-65°C, hydrogen at 7-8 kg/cmEXAMPLE 5 (according to the invention)Preparation of 3-amino-2, 2-dimethylpropanamideProduct of Example 4 was transferred into autoclave after dissolved in 840 ml of methanol- ammonia mixture (169 g of NH(2c) 3-Amino-2, 2-di(methyl)propionamide; A suspension of 2.5 g of 3-benzyloxycarbonylamino-2, 2-di(methyl)propionamide obtained in Reference Example (2b) (10 mmol) and 1.2 g of 7.5percent palladium-carbon (50percent wet) in ethanol (50 ml) was stirred under a hydrogen atmosphere at room temperature for two hours. Hydrogen in the reaction vessel was replaced by nitrogen. Then, palladium-carbon was separated by filtration and washed with ethanol. The solvent was evaporated under reduced pressure, and methylene chloride was added. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. n-Hexane was added to the residue, and the precipitated solid was collected by filtration to obtain 0.99 g of the title compound (yield: 85percent). Colorless solid. Example 5 (Step E); Methyl ester (5') (12.42 g, 74.09 mmol) was mixed with a solution of ammonia in methanol (22percent, 120 mL, 1.55 mot) at room temperature. The resulting solution was placed in an autoclave which was charged with additional gaseous ammonia. The mixture was heated to 60 °C and allowed to stir for 2 days at a pressure of 5 bar. The mixture was cooled to room temperature and the excess ammonia was released. The solvent was removed under reduced pressure to give 3-amino-2, 2-dimethyl-propionamide (3') as a solid in quantitative yield (10.94 g). H-NMR (300 MHz, DMSO-d(Step 8)Chloro pivalic amide (2') (5.0 g, 36.7 mmol) was placed in an autoclave and mixed with a solution of ammonia in methanol (2.4 M, 157 mL, 377 mmol) and a solution of sodium methoxide in methanol (30percent, 70 mL, 367 mmol). The autoclave was closed and the mixture was heated to 60 °C for 50 h. The mixture was cooled to room temperature, the overpressure was released and the suspension was filtered. The basic filtrate was neutralized (pH 7) by dropwise addition of HCI at 2-5

Reagent used in the synthesis of Aliskiren.

Molecular Weight:116.16
XLogP3:-0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:116.094963011
Monoisotopic Mass:116.094963011
Topological Polar Surface Area:69.1
Heavy Atom Count:8
Complexity:98.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes