5-Methyl-2-pyrazinecarboxylic acid → 2-Pyrazinecarboxylic acid, 5-methyl-, methyl ester

HRID 439907

Reaction equation

HRID 439907 reaction equation
NS(C1C=CC(CCN[C:14]([C:16]2[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=2)=[O:15])=CC=1)(=O)=O.CC1N=CC([C:30](O)=[O:31])=NC=1>CO>[CH3:30][O:31][C:14]([C:16]1[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 98835494-(2-(5-Methylpyrazine-2-carboxamido)ethyl)benzenesulfonamide

Product 1

HCID 4650652-Pyrazinecarboxylic acid, 5-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A process for the preparation of N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methylpyrazine-carboxamide of the formula I: ##STR21## consisting of: i) treating 5-methylpyrazine-2-carboxylic acid of the formula VIII: ##STR22## with methanol under reflux to obtain 5-methylpyrazine-2-carboxylic acid methyl ester of the formula VIII A: ##STR23## ii) reacting 5-methylpyrazine-2-carboxylic acid methyl ester of the formula VIII A with 2-phenylethylamine of the formula II: ##STR24## at 100° to 200° C. to obtain 5-methylpyrazine 2-(2-phenylethyl) carboxamide of the formula IX: ##STR25## 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: ##STR26## iv) and treating the [N-[2-[4-(chlorosulfonyl)phenyl]ethyl]-5-methyl purazinecarboxamide] 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-d948403bfd334ae58c8b8f8b1f3c072b
Source dataset
uspto-grants-1996_05
Patent number
US05516906

Linked notes

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