Tetrahydrofuran → 5-chloro-1-methyl-N-[3-[2-oxo-3-[[4-(2-pyrrolidin-1-ylethyl)anilino]methylidene]-1H-indole-6-carbonyl]phenyl]pyrazole-4-carboxamide

HRID 641040

반응식

HRID 641040 반응식
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:29])[C:27]=4[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].C1COCC1.[N:36]1([CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1>CCOC(C)=O.CCCCCC>[O:30]=[C:4]1[C:3](=[CH:2][NH:49][C:46]2[CH:47]=[CH:48][C:43]([CH2:42][CH2:41][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:44][CH:45]=2)[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:29])[C:27]=4[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5]1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)anilineHCID 178481853HCID 178481853, 화합물

생성물 1

HCID 1784818525-chloro-1-methyl-N-[3-[2-oxo-3-[[4-(2-pyrrolidin-1-ylethyl)anilino]methylidene]-1H-indole-6-carbonyl]phenyl]pyrazole-4-carboxamide수율 29%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

A small screw cap test tube was charged with 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 328, 100 mg, 0.2365 mmol) and THF (2.5 mL). To the resulting solution was added 4-(2-Pyrrolidin-1-yl-ethyl)-phenylamine (45 mg, 0.236 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and diluted with EtOAc (˜5 mL) and Hexane (˜50 mL). The precipitate that formed was collected by filtration and washed with acetone (˜15 mL) to afford the title compound in 29% yield (0.041 g, 0.0689 mmol).

후처리

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with acetone (˜15 mL)

출처 및 근거

ORD 기록
ord-3d7ee3e85c7d49b4a2ed2a20f30baa1c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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