Cesium carbonate → methyl 4-(4-(4-cyclopropyl-1H-imidazol-1-yl)picolinamido)thiophene-2-carboxylate

HRID 1423332노트

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HRID 1423332 반응식
F[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[S:14][CH:15]=2)=[O:9])[CH:3]=1.[CH:20]1([C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC>[CH:20]1([C:23]2[N:24]=[CH:25][N:26]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]4[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[S:14][CH:15]=4)=[O:9])[CH:3]=3)[CH:27]=2)[CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 58035636Methyl 4-(4-fluoropicolinamido)thiophene-2-carboxylateHCID 178420870HCID 178420870, 화합물

생성물 1

HCID 58035644methyl 4-(4-(4-cyclopropyl-1H-imidazol-1-yl)picolinamido)thiophene-2-carboxylate수율 74.5%

시약·촉매·용매 1

HCID 8008Butyronitrile용매

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온도
105 °C

실험 절차

To a solution of methyl 4-(4-fluoropicolinamido)thiophene-2-carboxylate (400 mg, 1.4 mmol) in butyronitrile (5 mL), was added 4-cyclopropyl imidazole (310 mg, 2.9 mmol), and caesium carbonate (840 mg, 2.6 mmol) and the reaction was heated to 105° C. for 2 hours. The reaction was filtered and the solids were washed with acetonitrile, methylene chloride, and the filtrate was evaporated under reduced pressure. The residue was suspended in acetonitrile, and the solids were collected by filtration to provide 384 mg (73%) of methyl 4-(4-(4-cyclopropyl-1H-imidazol-1-yl)picolinamido)thiophene-2-carboxylate. M+1=369.1

후처리

  1. filtrationThe reaction was filtered
  2. washthe solids were washed with acetonitrile, methylene chloride
  3. customthe filtrate was evaporated under reduced pressure
  4. filtrationthe solids were collected by filtration

출처 및 근거

ORD 기록
ord-d5ae6d386b634425979df1a41480ddef
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927582B2

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