HCID 14854959, compound → HCID 178493191, compound
Reaction equation
CS[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1.[NH2:10][C:11]1[C:31]([Cl:32])=[CH:30][C:14]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH2:27])[CH2:20][C@H:19]2[O:28][CH3:29])=[O:16])=[C:13]([O:33][CH3:34])[CH:12]=1>C(#N)C>[OH2:9].[NH2:10][C:11]1[C:31]([Cl:32])=[CH:30][C:14]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH:27][C:3]3[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=3)[CH2:20][C@H:19]2[O:28][CH3:29])=[O:16])=[C:13]([O:33][CH3:34])[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1.56 parts of 2-(methylthio)-4-pyrimidinol, 3.7 parts of cis-4-amino-N-[1-(3-aminopropyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide and 64 parts of acetonitrile was stirred for 40 hours at reflux temperature. Another portion of 0.7 parts of 2-(methylthio)-4-pyrimidinol was added and stirring was continued over weekend at reflux temperature. The reaction mixture was evaporated. The residue was taken up in trichloromethane. The whole was washed with water, saturated with ammonium hydroxide, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.82 parts (39.5%) of cis-4-amino-5-chloro-N-[1-[3-[(4-hydroxy-2-pyrimidinyl)amino]propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate; mp. 134.2° C. (compound 42).