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

HRID 77445

Reaction equation

HRID 77445 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f0de0ed6921f45e89569369893b53b05
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Linked notes

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