HCID 67345213, compound → HCID 67349888, compound

Reaction equation

[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:27]([C:28]#[C:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1>C(O)C.CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:27]([CH2:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1

Participants

Procedure

To a solution of methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbut-1-ynyl)benzoate (655 mg, 1.477 mmol) in ethanol (30 mL) and EtOAc (5 mL) was added palladium on activated carbon (10% wt., 400 mg). The reaction mixture was evacuated and backfilled with nitrogen gas. The reaction mixture was evacuated and backfilled with hydrogen gas. The reaction mixture was allowed to stir overnight at RT. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated. Ethanol (10 mL) and palladium on activated carbon (10% wt., 500 mg) were added. The reaction mixture was evacuated and backfilled with hydrogen and allowed to stir overnight at RT. The reaction mixture was filtered through a pad of celite. The solvent was removed under reduced pressure and methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbutyl)benzoate was obtained as a yellow-tan residue and used in the next reaction without further purification.