Dimethyl Sulfoxide → HCID 19080752, compound

HRID 963166Notes

Reaction equation

HRID 963166 reaction equation
N1C=CC=CC=1.CS(C)=O.Cl[S:12]([C:15]1[N:23]=[C:22]2[N:17]([C:18]([O:25][CH3:26])=[N:19][C:20]([CH3:24])=[CH:21]2)[N:16]=1)(=[O:14])=[O:13].[NH2:27][C:28]1[C:29]([C:36]([F:39])([F:38])[F:37])=[N:30][N:31]([CH2:34][CH3:35])[C:32]=1[CH3:33]>C(#N)C>[CH2:34]([N:31]1[C:32]([CH3:33])=[C:28]([NH:27][S:12]([C:15]2[N:23]=[C:22]3[N:17]([C:18]([O:25][CH3:26])=[N:19][C:20]([CH3:24])=[CH:21]3)[N:16]=2)(=[O:14])=[O:13])[C:29]([C:36]([F:38])([F:37])[F:39])=[N:30]1)[CH3:35]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 15003653HCID 15003653, compoundHCID 19080768HCID 19080768, compound

Product 1

HCID 19080752HCID 19080752, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine (0.32 g (4.0 mmol)) and dimethyl sulfoxide (0.03 g (0.4 mmol)) were added to a solution of 1.0 g (4.0 mmol) of 2-chlorosulfonyl-5-methoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine and 0.77 g (4.0 mmol) of 4-amino-1-ethyl-5-methyl-3-(trifluoromethyl)pyrazole in 15 mL of acetonitrile at ambient temperature with stirring. After 18 hours, the volatiles were removed by evaporation under reduced pressure and the residue was partitioned between dichloromethane and water, stirring for 10 min before separation. The solids were recovered by filtration and washed with ether. They were then resuspended in water and the mixture stirred for 30 min. The solids were recovered by filtration, washed with ether, and dried under reduced pressure at 40° C. overnight. The resulting 1.3 g (78 percent of theory) of white powder melting at 208°-209° C. was the title compound (Compound 1).

Workup

  1. customthe volatiles were removed by evaporation under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. stirringstirring for 10 min before separation
  4. filtrationThe solids were recovered by filtration
  5. washwashed with ether
  6. stirringthe mixture stirred for 30 min
  7. filtrationThe solids were recovered by filtration
  8. washwashed with ether
  9. customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-a1dd11aa331a496db92e3f7c5a150765
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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