Sodium Hydroxide → 2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1384211Notes

Reaction equation

HRID 1384211 reaction equation
[OH-].[Na+].C(OC([N:10]([C:29]1[C:34]([O:35][CH3:36])=[N:33][C:32]([CH3:37])=[CH:31][N:30]=1)[S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=O)C(C)C>CO>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([C:15]2[C:14]([S:11]([NH:10][C:29]3[C:34]([O:35][CH3:36])=[N:33][C:32]([CH3:37])=[CH:31][N:30]=3)(=[O:12])=[O:13])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:21][CH:22]=1)[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21186267N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Product 1

HCID 211862622-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M Sodium hydroxide solution (1 ml) was added to a solution of N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.7 g) in methanol (2 ml) and the reaction mixture stirred for 17 hours at ambient temperature. The methanol was removed by evaporation and water (20 ml) was added. The reaction mixture was extracted with ethyl acetate (4×15 ml), the combined organic extracts were dried (MgSO4) and then the solvent was removed by evaporation. The resultant oil was purified by eluting with 30% ethyl acetate/isohexane through a silica gel Mega Bond Elut column, followed by trituration with isohexane/diethyl ether to give 2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.4 g) as a solid, m.p. 70-72° C.; mass spectrum (+ve ESP): 399 (M+H)+.

Workup

  1. customThe methanol was removed by evaporation and water (20 ml)
  2. additionwas added
  3. extractionThe reaction mixture was extracted with ethyl acetate (4×15 ml)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customthe solvent was removed by evaporation
  6. customThe resultant oil was purified
  7. washby eluting with 30% ethyl acetate/isohexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-0d8a25aee69d4b808489d1f9bfc3a2da
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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