Potassium Carbonate → {3-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazole-4-carbonyl]-phenoxy}-acetic acid

HRID 251368

反応式

HRID 251368 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1.Cl[CH2:30][C:31]([O:33]C(C)(C)C)=[O:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([C:10](=[O:11])[NH:12][CH:13]3[CH2:14][CH2:15]3)[CH:16]=[CH:17][C:18]=2[CH3:19])[N:5]=[CH:4][C:3]=1[C:20]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[O:27][CH2:30][C:31]([OH:33])=[O:32])=[O:28]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 112458363-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

生成物 1

HCID 58088941{3-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazole-4-carbonyl]-phenoxy}-acetic acid収率 30.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (400 mg, 1.06 mmol) and t-butyl chloroacetate (319 mg, 2.12 mmol) in DMF (20 mL) was added K2CO3 (292 mg, 2.12 mmol) and the mixture was heated at 100° C. overnight. The solvent was removed, and the residue was suspended in EtOAc, washed by water, brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel (EtOAc:Hexane=3:1) to provide the product as a light yellow oil (140 mg, 27%).

後処理

  1. customThe solvent was removed
  2. washwashed by water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel (EtOAc:Hexane=3:1)

出典と根拠

ORDレコード
ord-8547416d67284b4798cdf7b14faa8336
出典データセット
uspto-grants-2011_01
特許番号
US07863314B2

関連ノート

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