Ethyl 4-amino-1-piperidinecarboxylate → Ethyl 4-[(thiazolo[4,5-c]pyridin-2-yl)amino]-1-piperidinecarboxylate
Reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CS([C:17]1[S:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=1)(=O)=O>ClC(Cl)Cl>[S:18]1[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=[C:17]1[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1Participants
4
Procedure
A mixture of 8.5 parts of ethyl 4-amino-1-piperidinecarboxylate and 2.6 parts of 2-(methylsulfonyl)thiazolo[4,5-c]pyridine was molten together for 1 hour at 120° C. After cooling, the mixture was taken up in trichloromethane. The whole was washed with water and sodium hydroxide, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in warm 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.8 parts (76%) of ethyl 4-[(thiazolo[4,5-c]-pyridin-2-yl)amino]-1-piperidinecarboxylate; mp. 213° C. (66).