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Acetonitrile → N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-2-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 870463
ノート
印刷プレビュー

反応式

HRID 870463 の反応式
[Cl:1][C:2]1[C:3](C(N)=O)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19](=[O:31])[N:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]([CH3:24])[C:22]=2[CH3:23])=[O:17])=[C:11]([F:32])[CH:10]=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.CC#[N:53]>CCOC(C)=O.O>[NH2:53][C:3]1[C:2]([Cl:1])=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[C:11]([F:32])[CH:10]=2)[CH:6]=[CH:5][N:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6342AcetonitrileHCID 76724Iodobenzene diacetateHCID 730510753-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

生成物 1

HCID 73053651N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-2-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide収率 47%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A suspension of 3-chloro-4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide (379 mg, 0.764 mmol) in EtOAc (4.5 mL), CH3CN (4.5 mL) and H2O (2.5 mL) was cooled and stirred at 0° C. for 30 minutes, then PhI(OAc)2 (295 mg, 0.917 mmol) was added and the mixture was stirred for another 30 minutes at 0° C., then allowed to warmed up to rt and stirred for another 10 hours. Filtered and the filter cake was washed with EtOAc (5 mL). The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=50/1) to give the title compound as a yellow solid (150 mg, 47.0%).

後処理

  1. temperaturewas cooled
  2. stirringthe mixture was stirred for another 30 minutes at 0° C.
  3. temperatureto warmed up to rt
  4. stirringstirred for another 10 hours
  5. filtrationFiltered
  6. washthe filter cake was washed with EtOAc (5 mL)
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=50/1)

出典と根拠

ORDレコード
ord-f5762c6ef80c45e78fbc2d436c77bf20
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08969388B1

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート