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

HRID 873006

反応式

HRID 873006 の反応式
[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)=[C:13]([F:27])[CH:12]=2)=[O:9])[C:4](=[O:28])[N:3]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CCOC(C)=O.CC#[N:58].O>>[NH2:58][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:28])[N:3]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[CH:12][C:13]=2[F:27])[CH:21]=[CH:20][N:19]=1

参加物

4

反応物 3

HCID 12217721Iodo benzene diacetateHCID 730532674-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamideHCID 86658869EtOAc CH3CN water

生成物 1

HCID 73053650N-(4-((2-aminopyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-c arboxamide収率 81%

実験手順

To a solution of 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide (2.5 g, 6.0 mmol) in EtOAc/MeCN/H2O (60 mL/60 mL/30 mL) was added iodobenzene diacetate (2.9 g, 9.0 mmol) at 0° C. The reaction was stirred at rt for 2 hours, then concentrated in vacuo. The resulted residue was dissolved with EtOAc (150 mL), washed with saturated aq. NaHCO3 (80 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was washed with DCM/ether (1/10, 22 mL) to give the title compound as a yellow solid (2.09 g, 81% yield).

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulted residue was dissolved with EtOAc (150 mL)
  3. washwashed with saturated aq. NaHCO3 (80 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with DCM/ether (1/10, 22 mL)

出典と根拠

ORDレコード
ord-4990648f024443a5add2446671749268
出典データセット
uspto-grants-2015_03
特許番号
US08975282B2

関連ノート

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