Dimethylcarbamoyl Chloride → 1,2,3,4-Tetrahydro-6((dimethylamino)carbonyl)oxy-2-N-(3-(2-thienyl)propionyl)isoquinoline
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1>[CH3:21][N:22]([CH3:26])[C:23]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12](=[O:20])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)=[O:24]Participants
4
Procedure
To a solution of the product of Example 14 (1.5 g) in pyridine (10 mL) at 0° C. was added dropwise dimethyl carbamyl chloride (0.52 mL) and the resulting solution was heated at 70°-80° C. for 24 hours. The pyridine was removed and the reaction diluted with CH2Cl2, washed with water (3x), brine, dried (MgSO4), filtered and concentrated. Chromatography of the residue on silica gel (elution with 1% CH2OH/CH2Cl2) provided 1.29 g of the desired product.