Ammonium Chloride → HCID 21186248, compound

HRID 1384210Notes

Reaction equation

HRID 1384210 reaction equation
C[O-].[Na+].[CH3:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([S:19]([N:22](C(OCC(C)C)=O)[C:23]3[C:28]([O:29][CH3:30])=[N:27][C:26]([CH3:31])=[CH:25][N:24]=3)(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)[CH3:6].[Cl-].[NH4+]>CO>[CH3:6][N:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([S:19]([NH:22][C:23]3[C:28]([O:29][CH3:30])=[N:27][C:26]([CH3:31])=[CH:25][N:24]=3)(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 21186304HCID 21186304, compound

Product 1

HCID 21186248HCID 21186248, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.115 g) was added to a solution of 2-[4-(N,N-dimethylamino)phenyl]-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.212 g) in methanol (10 ml) and the mixture was stirred and heated under reflux for 90 minutes. The reaction mixture was cooled, poured into saturated aqueous ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts were combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was triturated with ether to give 2-[4-(N,N-dimethylamino)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (104 mg) as a solid, m.p. 183-184.5° C.; 1H NMR (d6-DMSO): 2.2 (s, 3H), 2.95 (s, 6H), 3.8 (s, 3H), 6.7 (br s, 2H), 7.3-7.5 (m, 4H), 8.37 (dd, 1H), 8.7 (dd, 1H), 10.1 (br s, 1H); mass spectrum (+ve FAB, DMSO/methanol/NBA): 400 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 90 minutes
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-7d28395ead05457cb6b1cd58997b17da
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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