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

HRID 2352950노트

반응식

HRID 2352950 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:27]=[C:26]([CH2:28][CH3:29])[N:25]([CH3:30])[N:24]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:31].C1COCC1.[N:37]1([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1>CCOC(C)=O.CCCCCC>[O:31]=[C:4]1[C:3](=[CH:2][NH:49][C:46]2[CH:45]=[CH:44][C:43]([CH2:42][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:48][CH:47]=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:27]=[C:26]([CH2:28][CH3:29])[N:25]([CH3:30])[N:24]=4)=[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 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 1784366885-ethyl-N-[3-[3-(hydroxymethylidene)-2-oxo-1H-indole-6-carbonyl]phenyl]-1-methylpyrazole-3-carboxamide

생성물 1

HCID 1784366865-ethyl-1-methyl-N-[3-[2-oxo-3-[[4-(pyrrolidin-1-ylmethyl)anilino]methylidene]-1H-indole-6-carbonyl]phenyl]pyrazole-3-carboxamide수율 18%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

A small screw cap test tube was charged with 5-Ethyl-1-methyl-1H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 345, 70 mg, 0.1681 mmol) and THF (2.0 mL). To the resulting solution was added 4-Pyrrolidin-1-ylmethyl-phenylamine (30.1 mg, 0.171 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 (˜40 mL). The solid that precipitated was collected by filtration and washed with 0° C. iPrOH (˜10 mL) affording the title compound in 18% yield (0.018 g, 0.031 mmol).

후처리

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe solid that precipitated
  4. filtrationwas collected by filtration
  5. washwashed with 0° C. iPrOH (˜10 mL)

출처 및 근거

ORD 기록
ord-291df0816bf34962a4a0da13582589ee
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749530B2

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