Potassium Carbonate → HCID 21186226, compound

HRID 361427Notes

Reaction equation

HRID 361427 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([S:14]([N:17]([C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:18]3[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=3)(=[O:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.Br[CH:35]([CH3:40])[C:36]([O:38][CH3:39])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:30]([O:29][C:27]([N:17]([C:18]1[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=1)[S:14]([C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH:35]([C:36]([O:38][CH3:39])=[O:37])[CH3:40])=[CH:3][CH:4]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:16])=[O:15])=[O:28])[CH:31]([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 135810273HCID 135810273, compound

Product 1

HCID 21186226HCID 21186226, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(4-hydroxyphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.472 g), methyl 2-bromopropionate (217mg) and potassium carbonate (166 mg) in acetone (20 ml) was heated under reflux for 15 hours. Volatile material was removed by evaporation and water (25 ml) was added to the residue. The mixture was extracted with ethyl acetate (25 ml) and the extracts were washed with 2M sodium hydroxide solution (10 ml) and water (20 ml). The solution was dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give N-(isobutoxycarbonyl)-2-(4-[1-(methoxycarbonyl)ethoxy]phenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.32 g); 1H NMR (DMSO-d6): 0.6 (d, 6 H), 1.5-1.7 (m, 4 H), 2.5 (s, 3 H), 3.7 (s, 3 H), 3.8 (d, 2 H), 4.0 (s, 3 H), 5.1 (q, 1 H), 6.95 (d, 2 H), 7.5 (d, 2 H), 7.7-7.8 (m, 1 H), 8.2 (s, 1 H), 8.85 (d, 1 H), 8.9 (d, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customVolatile material was removed by evaporation and water (25 ml)
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with ethyl acetate (25 ml)
  6. washthe extracts were washed with 2M sodium hydroxide solution (10 ml) and water (20 ml)
  7. dry with materialThe solution was dried (MgSO4)
  8. customthe solvent was removed by evaporation
  9. customThe residue was purified by flash chromatography
  10. washeluting with ethyl acetate/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-92ac4120bbf54cd7b8fd7711aba946f1
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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