Reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2C(=[CH:13][CH:14]=[CH:15][CH:16]=2)NC=1)=[O:8].Cl[CH2:25][C:26]1N=[CH:29][O:28][N:27]=1.[C:31](#N)C.[CH3:34][N:35]([CH3:38])[CH:36]=O>>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:34](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:35]([CH2:38][C:26]2[CH:25]=[C:29]([CH3:31])[O:28][N:27]=2)[CH:36]=1)=[O:8]Participants
Conditions
- Temperature
- 80 °C
Procedure
26 mg (0.65 mmol) of sodium hydride (60%) was suspended in 3 mL of anhydrous dimethylformamide and to it was added 138.7 mg (0.50 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a and the resultant mixture was stirred at rt for 30 min. Then 77.4 mg (0.65 mmol) of 3-chloromethyl-1,2,4-oxadiazole was added to the reaction solution and the mixture was stirred at 80° C. for 1 h. The reaction solution was quenched by the addition of 10 mL of water. The crude product precipitated out of solution and was isolated by filtration. Purification of the crude product by flash chromatography provided 55 mg of 4cc as a colorless solid: LC-MSD, m/z for C23H20N2O3, [M+H]+=373.4, [M+2H]+=374.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time =2.639 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 2.36 (s, 3H), 5.38 (s, 2H), 5.90 (s, 1H), 7.15 (d, 1H), 7.42 (t, 1H), 7.50-7.68 (m, 4H), 8.27 (s, 1H), 8.44 (d, 1H).
Workup
- customThe reaction solution was quenched by the addition of 10 mL of water
- customThe crude product precipitated out of solution
- customwas isolated by filtration
- customPurification of the crude product by flash chromatography
- customprovided 55 mg of 4cc as a colorless solid
Sources & evidence
- ORD record
- ord-b1b7d3dc6c0d410b90c1fceaad4c1d8e
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Linked notes
Loading…