Reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[NH2:13][C:14]1[C:30]([Cl:31])=[CH:29][C:17]([C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]2[O:27][CH3:28])=[O:19])=[C:16]([O:32][CH3:33])[CH:15]=1.C1C=CC=CC=1>CO>[NH2:13][C:14]1[C:30]([Cl:31])=[CH:29][C:17]([C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][N:24]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=3)[CH2:23][C@H:22]2[O:27][CH3:28])=[O:19])=[C:16]([O:32][CH3:33])[CH:15]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 11 parts of 1-(4-fluorobenzoyl)aziridine, 6.28 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 45 parts of benzene and 20 parts of methanol was stirred and refluxed for 6 hours. The reaction mixture was evaporated and the residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 5.09 parts of cis-4-amino-5-chloro-N-[1-[2-[(4-fluorobenzoyl)amino]ethyl]-3-methoxy-4-piperidinyl]-2-methyoxybenzamide; mp. 208.7° C. (compound 131).
Workup
- temperaturerefluxed for 6 hours
- customThe reaction mixture was evaporated
- customthe residue was purified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (90:10 by volume as eluent
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe residue was crystallized from acetonitrile
Sources & evidence
- ORD record
- ord-a7fb1377e4c34c2494db76688d371a04
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05057525
Linked notes
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