Potassium Carbonate → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide

HRID 2382007ノート

反応式

HRID 2382007 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:17]1([NH2:26])[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[N:17]1([NH:26][C:14]([C:11]2[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:13][CH:12]=2)=[O:15])[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

生成物 1

HCID 250993572-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide収率 77.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (0.45 mmol) in EtOAc (8 mL) is added to a stirred solution of pyrrolo[3,2-b]pyridin-1-ylamine (0.45 mmol) and K2CO3 (0.45 mmol) in EtOAc (4 mL) and H2O (8 mL) at rt, and the reaction mixture is stirred at rt for 30 min. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide (116 mg, 77%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.60 (d, H) 7.15-7.60 (m, 4H), 8.01 (m, H), 8.10-8.41 (m, 3H), 9.27 (s, 2H), 12.45 (br, N—H). IC50=18 nM.

後処理

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration

出典と根拠

ORDレコード
ord-43b0fa9bfc384c69b0ed237aa200b5dc
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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