3-Fluorobenzylamine → tert-butyl (3aR,7aS)-2-[(3-fluorophenyl)methylamino]-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate

HRID 2053540

반응식

HRID 2053540 반응식
CS[C:3]1[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24]>ClCCl>[C:11]([O:10][C:8]([N:7]1[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=[C:3]1[NH:24][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([F:19])[CH:21]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 668533-FluorobenzylamineHCID 86596330cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic Acid, Tert-Butyl Ester

생성물 1

HCID 68569166tert-butyl (3aR,7aS)-2-[(3-fluorophenyl)methylamino]-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate수율 73.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), 3-fluorobenzylamine (0.5 mL, 4.4 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 188 mg of the product 191. 1H NMR (CDCl3) δ 8.56 (s, 1H), 7.45-7.20 (m, 3H), 7.20-6.95 (m, 2H), 5.20-4.95 (m, 2H), 4.35-4.10 (m, 2H), 2.75-2.55 (m, 1H), 2.20-2.05 (m, 1H), 1.80-1.05 (m, 15H); MS: m/z 348 (M++1).

후처리

  1. custom(reaction block) overnight
  2. temperatureThe reaction mixture is cooled to RT
  3. washwashed with 0.1N HCl, and brine
  4. customThe solvent is evaporated
  5. customthe residue triturated with EtOAc
  6. filtrationthe insoluble material filtered

출처 및 근거

ORD 기록
ord-8448ea54f8e04a0ea171287a58d8e708
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326792B2

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