Diisopropylamine → 6-[(cyclopropylmethyl)(propyl)amino]-N-1H-indol-4-ylpyrimidine-4-carboxamide

HRID 1746781ノート

反応式

HRID 1746781 の反応式
[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([OH:14])=O)[CH:7]=2)[CH2:3][CH2:2]1.C(Cl)(C(Cl)=O)=O.[NH:24]1[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([NH2:33])[C:27]=2[CH:26]=[CH:25]1.C(NC(C)C)(C)C>C(Cl)Cl.O.CN(C=O)C>[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:33][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[C:27]=3[CH:26]=[CH:25][NH:24]4)=[O:14])[CH:7]=2)[CH2:2][CH2:3]1

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 65578Oxalyl chlorideHCID 5834314-AminoindoleHCID 594470006-[(Cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylic acid2 回

生成物 1

HCID 594469506-[(cyclopropylmethyl)(propyl)amino]-N-1H-indol-4-ylpyrimidine-4-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A cooled (0° C.) solution of 6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxylic acid (Intermediate 21, 0.23 g; 0.98 mmol) in DCM (5 ml) was treated with DMF (1 drop of a 10% solution in DCM) followed by (COCl)2 (0.1 ml; 1.15 mmol). After stirring at 0° C. for 30 minutes, the mixture was treated with 1H-indol-4-amine (Aldrich, 146 mg; 1.1 mmol) and diisopropylamine (0.5 ml; 2.9 mmol). After stirring overnight, water was added and the layers separated. The organic phase was passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of Et2O to give the title compound as an off-white solid.

後処理

  1. stirringAfter stirring overnight
  2. customthe layers separated
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography (silica)
  5. washeluting with petroleum ether containing
  6. temperatureincreasing amounts of Et2O

出典と根拠

ORDレコード
ord-f148338a08e2441894667472a6181045
出典データセット
uspto-grants-2015_10
特許番号
US09150519B2

反応ノート

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