3-Methoxy-5-methyl-2-pyrazinamine → HCID 18704800, compound

HRID 343396Notes

Reaction equation

HRID 343396 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][C:6]=1[N+:21]([O-:23])=[O:22])[CH:2]([CH3:4])[CH3:3].[NH2:24][C:25]1[C:30]([O:31][CH3:32])=[N:29][C:28]([CH3:33])=[CH:27][N:26]=1>N1C=CC=CC=1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([S:17]([NH:24][C:25]3[C:30]([O:31][CH3:32])=[N:29][C:28]([CH3:33])=[CH:27][N:26]=3)(=[O:19])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][C:6]=1[N+:21]([O-:23])=[O:22])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 107018943-Methoxy-5-methyl-2-pyrazinamineHCID 18704790HCID 18704790, compound

Product 1

HCID 18704800HCID 18704800, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

4'-Isobutyl-3'-nitro-2-biphenylsulphonyl chloride (0.353 g) was added to a solution of 2-amino-3-methoxy-5-methylpyrazine (0.139 g) in pyridine (10 ml) at 0° C. The solution was heated at 75° C. for 18 hours and then volatile material was removed by evaporation. The residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column and the resulting foam was triturated with ether/hexane (1:1 v/v) to give 4'-isobutyl-N-(3-methoxy-5-methyl-2-pyrazinyl)-3'-nitro-2-biphenylsulphonamide (0.18 g), m.p. 114°-115° C.; mass spectrum (+ve CI): 457 (M+H)+.

Workup

  1. customvolatile material was removed by evaporation
  2. customThe residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column
  3. customthe resulting foam was triturated with ether/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-86af384f00234424b84c2ef0ab5c0a6c
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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