HCID 10910039, compound → HCID 57413701, compound
Reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH3:16])[C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[CH3:18][C:19]1[O:23][C:22]([CH2:24][CH2:25][C:26](Cl)=[O:27])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH3:16])[C:12]([NH:15][C:26](=[O:27])[CH2:25][CH2:24][C:22]3[O:23][C:19]([CH3:18])=[CH:20][CH:21]=3)=[N:13][CH:14]=2)=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-(4-(dimethylamino)phenyl)-3-methylpyridin-2-amine (120b, 2.27 g, 10.0 mmol) in pyridine (30 ml) was added with 3-(5-methylfuran-2-yl)propanoyl chloride (1.90 g, 11.0 mmol) and then stirred at room temperature for further 16 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give N-(5-(4-(Dimethylamino)phenyl)-3-methylpyridin-2-yl)-3-(5-methylfuran-2-yl) propanamide (120): 1H NMR (500 MHz, DMSO-d6):δ: 9.99 (s, 1H), 8.46 (s, 1H), 7.84 (s, 1H), 7.55 (m, 2H), 6.81 (m, 2H), 5.98 (s, 1H), 5.94 (s, 1H), 2.94 (s, 6H), 2.87 (t, 2H), 2.65 (t, 2H), 2.21 (s, 3H), 2.16 (s, 3H).