Pyridine → N-(2-carbamoylphenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748350ノート

反応式

HRID 1748350 の反応式
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.ClC(N(C)C)=C(C)C.[NH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31].N1C=CC=CC=1>C(Cl)Cl.O>[C:30]([C:29]1[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=1[NH:27][C:16]([C:13]1[CH:12]=[CH:11][C:10]2[CH:9]=[C:8]3[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]3[C:15]=2[CH:14]=1)=[O:18])(=[O:31])[NH2:32]

参加物

7

反応物 4

HCID 1049PyridineHCID 6942AnthranilamideHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2 回

生成物 1

HCID 57392346N-(2-carbamoylphenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide収率 27%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 100 mg, 0.41 mmol) in CH2Cl2 (1.5 mL) is added 1-chloro-N,N,2-trimethylpropenylamine (0.20 mL, 1.43 mmol). The reaction mixture is stirred for 5 h. 2-Aminobenzamide (200 mg, 1.47 mmol) and pyridine (0.12 mL, 1.48 mmol) are added and the reaction mixture is stirred for another 16 h at room temperature. Water (55 mL) is added and the resulting white solid is collected by filtration and purified by flash column chromatography using methanol in CH2Cl2 to afford the title compound (40 mg, 27%). LCMS (ESMS): m/z 363.61 (M+H+).

後処理

  1. stirringthe reaction mixture is stirred for another 16 h at room temperature
  2. filtrationthe resulting white solid is collected by filtration
  3. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-4d0d532378d341f5a587ee0f4b223950
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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