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

HRID 1746781노트

반응식

HRID 1746781 반응식
[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

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 65578Oxalyl chlorideHCID 5834314-AminoindoleHCID 594470006-[(Cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylic acid2회

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f148338a08e2441894667472a6181045
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150519B2

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