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

HRID 2053542

반응식

HRID 2053542 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][C:27]=1[F:28])[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][C:27]([F:28])=[C:20]([F:19])[CH:21]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 1235723,4-DifluorobenzylamineHCID 86596330cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic Acid, Tert-Butyl Ester

생성물 1

HCID 68568451tert-butyl (3aR,7aS)-2-[(3,4-difluorophenyl)methylamino]-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate수율 99.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of intermediate 76 (200 mg, 0.740 mmol), 3,4-difluorobenzylamine (0.5 mL, 4.2 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 270 mg of the product 195. 1H NMR (CDCl3) δ 8.60 (s, 1H), 7.40-7.10 (m, 3H), 5.15-4.90 (m, 2H), 4.30-4.10 (m, 2H), 2.70-2.55 (m, 1H), 2.20-2.05 (m, 1H), 1.85-1.10 (m, 15H); MS: m/z 366 (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-fa113969f68b491992ae24cb2125918a
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326792B2

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