Reaction equation
C(C1C(C)CN(C(NC[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)C1=C=O)C.[CH2:22]([CH:24]1[CH:28]([CH3:29])[CH2:27][N:26]([C:30]([NH:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([S:41]([NH2:44])(=[O:43])=[O:42])=[CH:37][CH:36]=2)=[O:31])[C:25]1=C=O)[CH3:23].ClS(O)(=O)=[O:49].N.[N-:53]=[C:54]=[O:55]>>[CH3:23][CH2:22][C:24]1[C:25](=[O:49])[N:26]([C:30]([NH:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([S:41]([NH:44][C:54]([NH:53][C@@H:17]3[CH2:16][CH2:15][C@@H:14]([CH3:13])[CH2:19][CH2:18]3)=[O:55])(=[O:42])=[O:43])=[CH:39][CH:40]=2)=[O:31])[CH2:27][C:28]=1[CH3:29]Participants
Procedure
U.S. Pat. No. 4,379,785 (hereinafter referred to as the '785 patent) discloses heterocyclic substituted sulfonylureas, particularly N-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-N′-4-methylcyclohexylurea i.e. glimepiride. The '785 patent teaches the preparation of glimepiride starting from 3-Ethyl-4-methyl-3-pyrrolidin-2-one and 2-phenylethylisocyanate to give [2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene. The [2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene is converted to the 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene sulfonamide, a compound of formula 4, by reacting with chlorosulfonic acid, followed by treatment with ammonia solution. This intermediate compound of formula 4 is further reacted with trans-4-methylyclohexyl isocyanate to form glimepiride. The '785 patent teaches a three step process for preparation of the intermediate compound of formula 4, i.e. 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene sulfonamide, which is represented in Scheme 1.
Sources & evidence
- ORD record
- ord-1314a1f00d504f6287bf8cbf7b56c169
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132444B2
Linked notes
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