Iodo benzene diacetate → N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 873015노트

반응식

HRID 873015 반응식
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18](C(N)=O)[CH:17]=3)=[CH:13][CH:12]=2)=[O:9])[C:4](=[O:27])[N:3]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CCOC(C)=O.CC#[N:57].O>>[NH2:57][C:18]1[CH:17]=[C:16]([O:15][C:14]2[CH:25]=[CH:26][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:27])[N:3]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[CH:12][CH:13]=2)[CH:21]=[CH:20][N:19]=1

참가 물질

4

반응물 3

HCID 12217721Iodo benzene diacetateHCID 86658869EtOAc CH3CN waterHCID 1178425924-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamid

생성물 1

HCID 73053608N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide수율 48%

실험 절차

To a solution of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamid (1.773 g, 3.998 mmol) in EtOAc/MeCN/H2O (20 mL/20 mL/10 mL) was added iodobenzene diacetate (1.6 g, 4.96 mmol) at 0° C. The reaction was stirred at rt overnight, then concentrated in vacuo and diluted with EtOAc (100 mL). The mixture was washed with saturated aq. NaHCO3 (60 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a yellow solid (799 mg, 48%).

후처리

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc (100 mL)
  3. washThe mixture was washed with saturated aq. NaHCO3 (60 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=30/1)

출처 및 근거

ORD 기록
ord-ae1dc14a7cee405da75969be0666aeb8
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975282B2

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