Dimethyl Sulfoxide → HCID 86729780, compound

HRID 2272624Notes

Reaction equation

HRID 2272624 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][CH:11]1[CH2:16][C:15](=[O:17])[O:14][C:13](=[O:18])[CH2:12]1.C1(C)C=CC=CC=1.CS(C)=O>O>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:15]([CH2:16][CH:11]([CH3:10])[CH2:12][C:13]([OH:18])=[O:14])=[O:17])=[CH:3][CH:4]=1)#[N:9]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 778283-Methylglutaric anhydrideHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 86729780HCID 86729780, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-aminopyridine-2-carbonitrile (300.0 mg, 2.518 mmol) and 4-methyldihydro-2H-pyran-2,6(3H)-dione (354.931 mg, 2.77 mmol) in a mixed solvent of toluene (7 mL) and DMSO (0.7 mL) was stirred at 110° C. for 16 hr. To the reaction mixture was added cold water, and the mixture was extracted with ethyl acetate (4×30 mL). The organic layer was washed with water, and dried, and the solvent was evaporated under reduced pressure. The obtained solid was washed with 50% dichloromethane/hexane solution to give 4-(6-cyanopyridin-3-ylcarbamoyl)-3-methylbutyric acid (300 mg, 48.2%) as a pale-yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×30 mL)
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. washThe obtained solid was washed with 50% dichloromethane/hexane solution

Sources & evidence

ORD record
ord-b2e84965bf1e47b0ad1af394ae39419a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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