Pyridine → 7-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335323노트

반응식

HRID 335323 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[F:23])[C:17](O)=[O:18])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.S(Cl)(Cl)=O.NC1C=C(C=CC=1F)C([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=1)=O.N1C=CC=CC=1>CO.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:17](=[O:18])[NH:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([F:42])=[C:38]([F:43])[CH:37]=4)[CH:20]=[CH:21][C:22]=3[F:23])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 615200303-Amino-N-(3,4-difluorobenzyl)-4-fluorobenzamideHCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2회

생성물 1

HCID 712831817-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture comprising 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1A step 3) (1.4 g, 5.81 mmol) and thionyl chloride (8.48 ml, 116 mmol) was heated at 100° C. for 1.5 hrs. The mixture was concentrated in vacuo. 3-Amino-N-(3,4-difluorobenzyl)-4-fluorobenzamide (step 1) (1.4 g, 5.00 mmol) and pyridine (16.65 ml) was added and the resulting suspension was stirred at RT for 1 hour. EtOAc and MeOH were added and the mixture was filtered. The white solid was dried to afford the title compound;

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationthe mixture was filtered
  3. customThe white solid was dried

출처 및 근거

ORD 기록
ord-f935efc185b349e6904eaccceb837846
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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