Pyrrolidine → Sunitinib

HRID 1008200

반응식

HRID 1008200 반응식
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH:15]=O)[NH:11][C:10]=1[CH3:17])=[O:8])[CH3:2].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2.N1CCCC1>C(O)C>[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12](/[CH:15]=[C:24]2\[C:25](=[O:30])[NH:26][C:27]3[C:23]\2=[CH:22][C:21]([F:20])=[CH:29][CH:28]=3)[NH:11][C:10]=1[CH3:17])=[O:8])[CH3:2]

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 20761785N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

생성물 1

HCID 5329102Sunitinib수율 88%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)-amide (809 g), 5-fluoro-1,3-dihydro-indol-2-one (438 g), ethanol (8000 mL) and pyrrolidine (13 mL) were heated at 78° C. for 3 hours. The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed with ethanol. The solids were stirred with ethanol (5900 mL) at 72° C. for 30 minutes. The mixture was cooled to room temperature. The solids were collected by vacuum filtration, washed with ethanol and dried under vacuum at 54° C. for 130 hours to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (1013 g, 88% yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 0.98 (t, 6H, 2×CH3), 2.43, 2.44 (2×s, 6H, 2×CH3), 2.50 (m, 6H, 3×CH2), 3.28 (q, 2H, CH2), 6.84, 6.92, 7.42, 7.71, 7.50 (5×m, 5H, aromatic, vinyl, CONH), 10.88 (s, 1H, CONH), 13.68 (s, 1H, pyrrole NH). MS m/z 397 [M−1].

후처리

  1. filtrationthe solids collected by vacuum filtration
  2. washwashed with ethanol
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with ethanol
  6. customdried under vacuum at 54° C. for 130 hours

출처 및 근거

ORD 기록
ord-4c9dad4817054d6e910d5a2ad607ba07
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06797725B2

연결된 노트

불러오는 중…