Methyl vinyl sulfone → HCID 59415936, 화합물

HRID 2061837노트

반응식

HRID 2061837 반응식
[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2].[CH:44]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH2:45]>C(O)(C)C>[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH2:45][CH2:44][S:46]([CH3:49])(=[O:48])=[O:47])[CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 19354Methyl vinyl sulfoneHCID 59415752HCID 59415752, 화합물

생성물 1

HCID 59415936HCID 59415936, 화합물수율 63.6%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
100 °C

실험 절차

(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydroquinoline-3-carboxylate (Example 262, 0.150 g, 0.24 mmol) was taken up in isopropanol (2 mL) and methyl vinyl sulfone (0.026 mL, 0.29 mmol) was added. The reaction mixture was stirred at 100° C. for 18 h in a sealed vessel, then cooled to room temperature and the solvent was removed in vacuo and loaded directly onto silica. Purified by flash column chromatography on silica gel using (dichloromethane-methanol) gave (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-(2-(methylsulfonyl)ethyl)piperidin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.110 g, 62.5%).

후처리

  1. temperaturecooled to room temperature
  2. customthe solvent was removed in vacuo
  3. customPurified by flash column chromatography on silica gel using (dichloromethane-methanol)

출처 및 근거

ORD 기록
ord-b2f0a653cfb945a5be81474f3a08aa80
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

반응 노트

불러오는 중…