4-(Aminomethyl)benzonitrile → (7aS,6S)-4-{[2-(3,5-dichloro-phenyl)-1,3-dioxo-hexahydro-pyrrolo[1,2-c]imidazol-6-ylamino]-methyl}-benzonitrile

HRID 49985

반응식

HRID 49985 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C:16](=O)[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)#[N:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@H:16]([NH:27][CH2:26][C:25]4[CH:28]=[CH:29][C:22]([C:20]#[N:21])=[CH:23][CH:24]=4)[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 826084-(Aminomethyl)benzonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 21301015(7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione

생성물 1

HCID 21300996(7aS,6S)-4-{[2-(3,5-dichloro-phenyl)-1,3-dioxo-hexahydro-pyrrolo[1,2-c]imidazol-6-ylamino]-methyl}-benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound of formula (In), wherein R11 is 4-cyano, m is 1, W=NH, and the bonds depicted as wavy bonds define the 7aS,6S stereoisomer, was prepared as follows. To a solution of (7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione (0.5 g) (0.0017 mol) (Preparation 20), in 50 mL of DCM was added molecular sieves 4A, 4-cyanobenzyl amine (0.27 g) (0.002 mol), then NaBH(OAc)3 (0.54 g) (0.00255 mol.). The reaction mixture was stirred overnight at RT and then the insoluble material eliminated. After evaporating the solvent, the residue was purified by SiO2 chromatography (eluent: DCM/MeOH 98/2) to afford the titled compound and its stereoisomer. 7aS,6S stereoisomer (70 mg). NMR (CDCl3, 200 MHz): 7.45 (2H, d), 7.3 (1H, m), 7.2-7.1(4H, m), 4.25 (1H, dd), 4.05 (1H, d), 3.65 (2H, dd), 3.4(1H, m), 3.02 (1H, dd), 2.35-2.2 (1H, m), 2.0 (1H, bd).

후처리

  1. customwas prepared
  2. customAfter evaporating the solvent
  3. customthe residue was purified by SiO2 chromatography (eluent: DCM/MeOH 98/2)

출처 및 근거

ORD 기록
ord-d36fbc0a06ef48a49fc3e81ba82b11d6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

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