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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(4-((7-(2-hydroxypropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2277392
ノート
印刷プレビュー

反応式

HRID 2277392 の反応式
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C@H:19]([OH:21])[CH3:20])=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:24][N:25]1[C:29]([CH3:30])=[C:28]([C:31](O)=[O:32])[C:27](=[O:34])[N:26]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[OH:21][C@H:19]([CH3:20])[CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:31]([C:28]4[C:27](=[O:34])[N:26]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:25]([CH3:24])[C:29]=4[CH3:30])=[O:32])=[CH:23][CH:22]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][CH:14]=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

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 68193946(R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol

生成物 1

HCID 60172730(R)-N-(4-((7-(2-hydroxypropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide収率 14.3%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
43 °C

実験手順

To a solution of (R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol (2.5 g, 11.9 mmol), 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (2.0 g, 8.6 mmol) and HOAT (0.2 g, 1.6 mmol) in DCM (35 mL) was added EDCI (1.9 g, 9.7 mmol). The reaction mixture was stirred at 43° C. for 12 hours, then cooled to room temperature and diluted with a mixture of DCM and H2O (50 mL/50 mL). The organic phase was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a column chromatography on silica gel (EtOAc) to afford the title compound as a yellow solid (0.6 g, 14.3%).

後処理

  1. temperaturecooled to room temperature
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a column chromatography on silica gel (EtOAc)

出典と根拠

ORDレコード
ord-dbe2299a314547f489025eb3e15eb38b
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133162B2

反応ノート

読み込み中…

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