Pyridine → 5-(5-bromo-2-chlorobenzamido)-N-cyclopropyl-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522126

反応式

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([C:21]([OH:23])=O)[CH:11]=1)=[O:8].[CH:26]1([NH2:29])[CH2:28][CH2:27]1.N1C=CC=CC=1.CCCP(O)(O)=O.C(=O)([O-])[O-].[K+].[K+]>CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:13]=[C:12]([C:21]([NH:29][CH:26]2[CH2:28][CH2:27]2)=[O:23])[CH:11]=1)=[O:8]

参加物

実験手順

To 5-(5-bromo-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Preparation 12, 200 mg, 0.48 mmol), cyclopropylamine (137 mg, 2.40 mmol) and pyridine (114 mg, 1.44 mmol) in methyl THF (5 mL) was added 1-propylphosphonic acid cyclic anhydride (50% solution in EtOAc, 0.48 mL, 0.82 mmol) at room temperature. The reaction was stirred at room temperature for 17 hours. A 2M aqueous solution of potassium carbonate was added until the pH became basic and the solution was extracted with EtOAc (3×15 mL). The combined organic layers were concentrated in vacuo and the residue was purified by silica gel column chromatography eluting with EtOAc to afford the title compound (290 mg, 88%).

後処理

extractionthe solution was extracted with EtOAc (3×15 mL)
concentrationThe combined organic layers were concentrated in vacuo
customthe residue was purified by silica gel column chromatography
washeluting with EtOAc

出典と根拠

ORDレコード: ord-05189135f75246cd9c30df9d9100c3b1
出典データセット: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09328096B2

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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