Methanol → 2-[4-(2-carboxyvinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1107493Notes

Reaction equation

HRID 1107493 reaction equation
O.[OH-].[Li+].C(OC([N:11]([C:33]1[C:38]([O:39][CH3:40])=[N:37][C:36]([CH3:41])=[CH:35][N:34]=1)[S:12]([C:15]1[C:16]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29]([O:31]C)=[O:30])=[CH:23][CH:22]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13])=O)C(C)C.CO>O>[C:29]([CH:28]=[CH:27][C:24]1[CH:25]=[CH:26][C:21]([C:16]2[C:15]([S:12]([NH:11][C:33]3[C:38]([O:39][CH3:40])=[N:37][C:36]([CH3:41])=[CH:35][N:34]=3)(=[O:13])=[O:14])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:22][CH:23]=1)([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 54341699HCID 54341699, compound

Product 1

HCID 537886522-[4-(2-carboxyvinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (87 mg) was added to a solution of N-isobutoxycarbonyl-2-[4-(2-[methoxycarbonyl]vinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (250 mg) in tetrahydrefuran (6.2 ml) followed by methanol (2.5 ml) and water (2.5 ml). The reaction mixture was stirred at ambient temperature for 18 hours then evaporated to dryness. The residue was dissolved in water (50 ml), washed with ethyl acetate (50 ml), acidified with 8% aqueous citric acid to pH 3-4 and extracted with ethyl acetate (100 ml). The organic layer was extracted with saturated sodium bicarbonate solution (50 ml) and the aqueous phase separated, acidified with 8% aqueous citric acid and extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried (MgSO4) and evaporated to give 2-[4-(2-carboxyvinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (108 mg) as a solid, m.p. 233-235° C.: 1H NMR (d6 -DMSO): 2.2 (s, 3H), 3.8 (s, 3H), 6.55 (d, 1H), 7.35 (br s, 1H), 7.45 (d, 2H), 7.55-7.75 (m, 4H), 8.45 (dd, 1H), 8.8 (dd, 1H), 10.1 (br s, 1H); mass spectrum (+ve ESP) 427 (M+H)+.

Workup

  1. customthen evaporated to dryness
  2. dissolutionThe residue was dissolved in water (50 ml)
  3. washwashed with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (100 ml)
  5. extractionThe organic layer was extracted with saturated sodium bicarbonate solution (50 ml)
  6. customthe aqueous phase separated
  7. extractionextracted with ethyl acetate (3×30 ml)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-9af98156d2fb491c983bc95cfcb497c1
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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