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

HRID 2382007

반응식

HRID 2382007 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-43b0fa9bfc384c69b0ed237aa200b5dc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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