1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamide

HRID 520678

反応式

HRID 520678 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25](O)=[O:26])[C:21](=[O:28])[N:20]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.O>[CH3:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25]([NH:1][C:2]2[N:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=3)=[CH:4][CH:3]=2)=[O:26])[C:21](=[O:28])[N:20]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 90031028HCID 90031028、化合物

生成物 1

HCID 730532664-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamide収率 25%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
45 °C

実験手順

To a suspension of 4-((6-aminopyridin-3-yl)oxy)picolinamide (230 mg, 1 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (237 mg, 1.02 mmol) in DCM (5 mL) was added EDCI (230 mg, 1.2 mmol) and HOAT (27 mg, 0.2 mmol). The reaction was stirred at 45° C. for 28 hours, then cooled to rt and diluted with water (10 mL) and DCM (20 mL). The organic phase was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1) to give the title compound as a light grey solid (111 mg, 25%).

後処理

  1. temperaturecooled to rt
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1)

出典と根拠

ORDレコード
ord-1619e4cb056440a19f65efca89f1c326
出典データセット
uspto-grants-2016_05
特許番号
US09326975B2

関連ノート

読み込み中…