Acetic Acid → HCID 21186284, compound

HRID 1107495Notes

Reaction equation

HRID 1107495 reaction equation
[O:1]([CH2:9][CH:10]([CH3:37])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([S:24]([NH:27][C:28]3[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)[Si](C(C)(C)C)(C)C.C(=O)([O-])O.[Na+].[C:43](O)(=[O:45])[CH3:44]>C(OC(=O)C)(=O)C>[C:43]([O:1][CH2:9][CH:10]([CH3:37])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([S:24]([NH:27][C:28]3[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=3)(=[O:25])=[O:26])=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:16][CH:17]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 21186331HCID 21186331, 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 6 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 purified 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. customThe residue was purified 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-64f04ccd2fda4fe4905800329f8057d5
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

Loading…