Dimethyl Sulfoxide → HCID 86729782, compound

HRID 2272626Notes

Reaction equation

HRID 2272626 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=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:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:15]([CH2:16][CH:11]([CH3:10])[CH2:12][C:13]([OH:18])=[O:14])=[O:17])=[N:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 778283-Methylglutaric anhydrideHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 86729782HCID 86729782, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-aminonicotinonitrile (100.0 mg, 0.839 mmol) and 4-methyldihydro-2H-pyran-2,6(3H)-dione (118 mg, 0.923 mmol) in a mixed solvent of toluene (3 mL) and DMSO (0.3 mL) was stirred at 120° C. for 24 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-(5-cyanopyridin-2-ylcarbamoyl)-3-methylbutyric acid (30 mg, 14.49%) 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-ab1744b9e94140ad99884233c8cdbbf8
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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