Cesium carbonate → 6-((6-(3,4-dichlorobenzylamino)pyridin-3-yl)methoxy)quinolin-2(1H)-one

HRID 77445ノート

反応式

HRID 77445 の反応式
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[N:7][CH:8]=1.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH:24]=[CH:23]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Cl:18][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[Cl:17])[CH2:10][NH:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[NH:26][C:25](=[O:30])[CH:24]=[CH:23]3)=[CH:4][CH:5]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 1770652,6-DihydroxyquinolineHCID 866797295-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine

生成物 1

HCID 866797306-((6-(3,4-dichlorobenzylamino)pyridin-3-yl)methoxy)quinolin-2(1H)-one収率 26%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine (0.1 g, 0.332 mmol), 6-hydroxyquinolin-2(1H)-one (0.048 g, 0.298 mmol) and Cs2CO3 (0.864 g, 2.65 mmol) in DMF (3.3 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and the resulting suspension was filtered. The filter cake was stirred in methanol for 1 h, filtered, washed with methanol, and dried to yield 6-((6-(3,4-dichlorobenzylamino)pyridin-3-yl)methoxy)quinolin-2(1H)-one as a beige solid (0.033 g, 22%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.65 (1H, s), 8.06 (1H, d, J=2.01 Hz), 7.85 (1H, d, J=9.54 Hz), 7.46-7.63 (3H, m), 7.08-7.37 (5H, m), 6.39-6.62 (2H, m), 4.91 (2H, s), 4.49 (2H, d, J=6.02 Hz). LCMS: R.T.=3.15; [M+H]+=426.00.

後処理

  1. filtrationthe resulting suspension was filtered
  2. stirringThe filter cake was stirred in methanol for 1 h
  3. filtrationfiltered
  4. washwashed with methanol
  5. customdried

出典と根拠

ORDレコード
ord-f0de0ed6921f45e89569369893b53b05
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

反応ノート

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