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 641018ノート

反応式

HRID 641018 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d6e4f936e9e040929d7eaf5f3c0d06f4
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

反応ノート

読み込み中…