Water → N-[(3R,6S)-6-(2,3-Difluorophenyl)-2-thioxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

HRID 14397

반응식

HRID 14397 반응식
C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=2[F:23])[CH2:12][N:11]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:10]1=[S:29].[O:30]=[C:31]1[NH:39][C:34]2=[N:35][CH:36]=[CH:37][CH:38]=[C:33]2[N:32]1[CH:40]1[CH2:45][CH2:44][N:43]([C:46](Cl)=[O:47])[CH2:42][CH2:41]1.O>ClCCl>[F:23][C:17]1[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:16]=1[C@H:13]1[CH2:12][N:11]([CH2:24][C:25]([F:27])([F:28])[F:26])[C:10](=[S:29])[C@H:9]([NH:8][C:46]([N:43]2[CH2:42][CH2:41][CH:40]([N:32]3[C:33]4[C:34](=[N:35][CH:36]=[CH:37][CH:38]=4)[NH:39][C:31]3=[O:30])[CH2:45][CH2:44]2)=[O:47])[CH2:15][CH2:14]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 222932214-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chlorideHCID 86616757(3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepane-2-thione

생성물 1

HCID 86616758N-[(3R,6S)-6-(2,3-Difluorophenyl)-2-thioxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide수율 55.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (100 μL, 0.720 mmol) was added to a solution of the bis hydrochloride salt of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepane-2-thione (90 mg, 0.240 mmol) and 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chloride (74 mg, 0.264 mmol) in dichloromethane (10 mL) and the mixture heated to reflux. After 18 h, the reaction was allowed to cool to ambient temperature, water was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (78 mg). MS 583.2 (M+1).

후처리

  1. temperaturethe mixture heated to reflux
  2. extractionthe mixture was extracted with dichloromethane (3×)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-aa1b893dcf154e85b3ad2cfec0553e85
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732438B2

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