Nicotinic Acid → HCID 20098208, compound

HRID 1768921Notes

Reaction equation

HRID 1768921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14](O)=[O:15])=[C:12]([S:17][C:18]3[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=3)[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[H-].[Na+].[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44].C(=C1N=CC=N1)=O.C(O)(=O)C1C=CC=NC=1>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([NH:46][S:43]([CH3:42])(=[O:45])=[O:44])=[O:15])=[C:12]([S:17][C:18]3[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=3)[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 938Nicotinic AcidHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 13571086CarbonylimidazoleHCID 200952664-(3-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid

Product 1

HCID 20098208HCID 20098208, compoundYield 328.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 3.0 g (0.0074 mol) of 4-(3-chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid in 30 ml of N,N-dimethylformamide was added 1.50 g (0.0093 mol) of carbonyldiimidazole with stirring, and the mixture was stirred at room temperature for 24 hours. To a suspension of 0.60 g (0.0015 mol) of 60% sodium hydride in 30 ml of N,N-dimethylformamide was added 1.8 g (0.0019 mol) of methanesulfonamide and stirred at 80° C. for 2 hours. Thereafter, the above prepared N,N-dimethylformamide solution of carbonylimidazole of nicotinic acid was added thereto at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was then poured into water, and washed with 50 ml of ethyl acetate. Thereafter, the aqueous layer was acidified with 10% HCl, and extracted with 100 ml of ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, filtrated and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/1) to obtain 3.0 g of a light-yellowish glass-like aimed product.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. stirringstirred at 80° C. for 2 hours
  3. additionwas added
  4. stirringat room temperature, and the mixture was stirred at 80° C. for 2 hours
  5. washwashed with 50 ml of ethyl acetate
  6. extractionextracted with 100 ml of ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  9. filtrationfiltrated
  10. concentrationconcentrated
  11. customThe concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-325371cc6dce450abda683c966a175f8
Source dataset
uspto-grants-1995_01
Patent number
US05380700

Reaction notes

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