Acetic Acid → HCID 21186284, compound

HRID 1384244Notes

Reaction equation

HRID 1384244 reaction equation
[OH:1][CH2:2][CH:3]([CH3:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([S:17]([NH:20][C:21]3[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=3)(=[O:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+].[C:36](O)(=[O:38])[CH3:37]>C(OC(=O)C)(=O)C>[C:36]([O:1][CH2:2][CH:3]([CH3:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([S:17]([NH:20][C:21]3[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=3)(=[O:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 21186225HCID 21186225, compound

Product 1

HCID 21186284HCID 21186284, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-[4-(3-hydroxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide from Example 19 (100 mg) was heated in a mixture of acetic acid (0.5 ml) and acetic anhydride (0.5 ml) to 80° C. for 10 minutes and allowed to cool to ambient temperature. After 16 hours excess saturated aqueous sodium hydrogen carbonate was added cautiously and the product extracted into ethyl acetate (3×20 ml). The combined organic extract was dried (MgSO4) and evaporated. The residue was purifed by elution with a gradient of 0-30% ethyl acetate/hexane through a silica gel Mega Bond Elut column (1 g) to give 2-[4-(3-acetoxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (70 mg) as a white foam; 1H NMR (CDCl3): 0.98 (d, 3H), 1.58 (s, 3H), 2.11 (s, 3H), 2.1-2.3 (m, 1H), 2.51 (q, 1H), 2.85 (q, 1H), 3.80 (s, 3H), 3.97 (m, 2H), 6.69 (s, 1H), 7.2 (d, 2H), 7.29 (d, 2H), 8.67 (d, 1H), 8.80 (dd, 1H); mass spectrum (+ve ESP): 471.1 (M+H)+.

Workup

  1. extractionthe product extracted into ethyl acetate (3×20 ml)
  2. extractionThe combined organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. washThe residue was purifed by elution with a gradient of 0-30% ethyl acetate/hexane through a silica gel Mega Bond Elut column (1 g)

Sources & evidence

ORD record
ord-fedaa8e3aacf48cbb76df85a0f639dad
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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