Potassium Carbonate → HCID 136262645, compound

HRID 591671Notes

Reaction equation

HRID 591671 reaction equation
[CH2:1]([N:8]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([C:25]2[NH:34][C:33](=[O:35])[C:32]3[C:27](=[CH:28][C:29]([O:38][CH3:39])=[CH:30][C:31]=3[O:36][CH3:37])[N:26]=2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]([CH:12]1[CH2:17][CH2:16][N:15]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[NH:34][C:33](=[O:35])[C:32]4[C:27](=[CH:28][C:29]([O:38][CH3:39])=[CH:30][C:31]=4[O:36][CH3:37])[N:26]=3)=[CH:23][N:24]=2)[CH2:14][CH2:13]1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21250987HCID 21250987, compoundHCID 136415074HCID 136415074, compound

Product 1

HCID 136262645HCID 136262645, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-N-(piperidin-4-yl)acetamide (1.5 g, 6.3 mmol) and 2-(6-chloropyridin-3-yl)-5,7-dimethoxyquinazolin-4(3H)-one (1.0 g, 3.2 mmol) in DMF (15 mL) was added K2CO3 (0.875 g, 6.3 mmol) and the reaction was heated at reflux temperature overnight. The resulting mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, to afford the title compound (0.500 g, 30%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.84 (s, 1H), 8.86 (s, 1H), 8.22 (d, J=9.2 Hz, 1H), 7.33-7.37 (m, 1H), 7.14-7.27 (m, 4H), 6.88-6.96 (m, 1H), 6.66 (d, J=1.5 Hz, 1H), 6.46 (d, J=1.5 Hz, 1H), 4.44-4.58 (m, 4.5H), 4.10-4.20 (m, 0.5H), 3.87 (s, 3H), 3.83 (s, 3H), 2.86-2.98 (m, 2H), 2.25 (s, 1.5H), 1.95 (s, 1.5H), 1.45-1.77 (m, 4H). ESI/APCI MS m/z 514 [M+H]+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux temperature overnight
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel
  5. washeluting with 1% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c4e4d5ff371040f28cfe40b50f7bd488
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…