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【结 构 式】

【分子编号】21321

【品名】(3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

【CA登记号】

【 分 子 式 】C16H15N3O

【 分 子 量 】265.31472

【元素组成】C 72.43% H 5.7% N 15.84% O 6.03%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

2-Aminobenzophenone (I) is acylated with bromoacetyl bromide followed by reaction with ammonia to form the [1,4]benzodiazepine. N1-Methylation produces 1,3-dihydro-1-methyl-5-phenyl-2H-[1,4]benzodiazepin-2-one (II). Treatment with isoamyl nitrate and t-BuOK gives an oxime, which is reduced by catalytic hydrogenation to racemic 3-amino-benzodiazepine (III), which is isolated as the crystalline benzenesulfonic acid salt. Crystallization-induced asymmetric transformation yields 3(S)-(-)-3-amino-1,3-dihydro-1-methyl-5-phenyl-2H-[1,4]benzodiazepin-2-one (IV). Acylation with indole-2-carbonylimidazolide produces MK-329.

1 Reider, P.J.; Davis, P.; Grabowski, E.J.J.; Hughes, D.L.; Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonis. J Org Chem 1987, 52, 955.
2 Freidinger, R.M.; Berlin, R.G.; MK-329. Drugs Fut 1989, 14, 9, 862.
3 Veber, D.F.; Freidinger, R.M.; Hirshfield, J.; Rittle, K.E.; Springer, J.P.; DiPardo, R.M.; Bock, M.G.; Evans, B.E.; Synthesis and resolution of 3-amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones. J Org Chem 1987, 52, 3232.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 21101 (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone 2835-77-0 C13H11NO 详情 详情
(II) 21319 1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one C16H14N2O 详情 详情
(III) 21320 3-Amino-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one benzenesulfonate C22H21N3O4S 详情 详情
(IV) 21321 (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one C16H15N3O 详情 详情
(V) 14005 2-Bromoacetyl bromide; Bromoacetyl bromide 598-21-0 C2H2Br2O 详情 详情
(VI) 21323 3,5-dichloro-2-hydroxybenzaldehyde; 3,5-Dichlorosalicylaldehyde 90-60-8 C7H4Cl2O2 详情 详情
(VII) 21324 1H-imidazol-1-yl(1H-indol-2-yl)methanone C12H9N3O 详情 详情
Extended Information