Dimethyl Sulfoxide → HCID 71765148, compound

HRID 2272983Notes

Reaction equation

HRID 2272983 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20](C(=O)C(F)(F)F)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]#[N:10].C(=O)([O-])[O-:30].[K+].[K+].CS(C)=O.OO>CO.O>[NH:20]1[CH2:21][CH2:22][CH:17]([C:14]2[CH:15]=[CH:16][C:11]([C:2]3[NH:10][C:9](=[O:30])[C:5]4[N:4]([CH:8]=[CH:7][CH:6]=4)[CH:3]=3)=[CH:12][CH:13]=2)[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen Peroxide2×HCID 11430Potassium CarbonateHCID 89826290HCID 89826290, compound

Product 1

HCID 71765148HCID 71765148, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(2-Oxo-2-{4-[1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl]-phenyl}-ethyl)-1H-pyrrole-2-carbonitrile (1.40 g; 3.60 mmol) is slurried in methanol (10 ml). Potassium carbonate (2.49 g; 17.98 mmol), dry dimethylsulfoxide (0.77 ml; 10.79 mmol) and hydrogen peroxide (1.10 ml; 10.79 mmol) are added (caution: strong exothermic reaction after the addition of hydrogen peroxide). The yellow suspension is stirred overnight. The reaction mixture is diluted with water, the precipitate is filtered off by suction, washed with water and dried under vacuum at 50° C. The crude product is purified by flash chromatography. The combined fractions are evaporated to dryness. The residue is triturated with diethylether, filtered off by suction and dried under vacuum at 50° C. to afford 3-(4-piperidin-4-yl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one as off-white solid;

Workup

  1. customstrong exothermic reaction
  2. filtrationthe precipitate is filtered off by suction
  3. washwashed with water
  4. customdried under vacuum at 50° C
  5. customThe crude product is purified by flash chromatography
  6. customThe combined fractions are evaporated to dryness
  7. customThe residue is triturated with diethylether
  8. filtrationfiltered off by suction
  9. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-ab758f9f5ad24676bdc51d1693095493
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

Loading…