Methanol → (r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

HRID 1531302노트

반응식

HRID 1531302 반응식
COC([NH:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:19]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=2)[CH2:7]1)=O.I[Si](C)(C)C.CO>C(#N)C>[NH2:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:19]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=4)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=2)[CH2:7]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 9869236(r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

생성물 1

HCID 11112358(r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

(R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide (6.5 g, 13.9 mmol) is dissolved in acetonitrile (325 mL) and cooled to 0° C. under nitrogen. Iodotrimethylsilane (11.1 g, 55.6 mmol) is added dropwise, the mixture is allowed to warm to room temperature and is stirred overnight. Methanol (100 mL) is added and the mixture is stirred for 1 hour and then concentrated in vacuo. The residue is dissolved in ethyl acetate (750 mL) and washed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL). The organic phase is dried over sodium sulfate and concentrated to afford (R)-N-(2-aminoindan-5-yl)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxamide.

후처리

  1. temperatureto warm to room temperature
  2. stirringthe mixture is stirred for 1 hour
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate (750 mL)
  5. washwashed with saturated sodium bicarbonate (2×125 mL), water (125 mL), 5% Na2S2O3 solution (125 mL), water (125 mL), and brine (50 mL)
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-83a6e129983c47cb8a982d0ea0105919
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197798B1

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