Ammonia → 4-(2-(5-Methylpyrazine-2-carboxamido)ethyl)benzenesulfonamide
Reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=2)=[O:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH3:23]>>[NH2:23][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]2[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=2)=[O:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3]Participants
Procedure
According to the invention there is provided a process for the preparation of N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methylpyrazine-carboxamide of the formula I: ##STR15## consisting of: i) treating 5-methylpyrazine-2-carboxylic acid of the formula VIII: ##STR16## with methanol under reflux to obtain 5-methylpyrazine-2-carboxylic acid methyl ester of the formula VIII A ##STR17## ii) reacting 5-methylpyrazine-2-carboxylic acid methyl ester of the formula VIII A with 2-phenylethylamine of the formula II: ##STR18## at 100° to 200° C. to obtain 5-methylpyrazine 2-(2-phenylethyl) carboxamide of the formula IX: ##STR19## iii) chlorosulfonating the 5-methylpyrazine-2(2-phenylethyl)carboxamide of the formula IX with chlorosulfonic acid at 0°-45° C. to obtain [N-[2-[4-Chlorosulfonyl)phenyl]ethyl]-5-methylpyrazine carboxamide] of the formula X: ##STR20## iv) and treating the (N-[2-[4-(chlorosulfonyl)phenyl]ethyl]-5-methyl pyrazine-carboxamide] of the formula X with ammonia to obtain N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methylpyrazine carboxamide of the formula I.
Sources & evidence
- ORD record
- ord-56eccb1263074b76be970c22a7b7f1ea
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05516906
Reaction notes
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