Dimethyl Sulfoxide → HCID 69416617, compound

HRID 1592922Notes

Reaction equation

HRID 1592922 reaction equation
CS(C)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:18]=3)=[CH:15][N:14]([C:29]3[CH:34]=[CH:33][C:32](=[O:35])[NH:31][N:30]=3)[N:13]=2)=[CH:8][CH:7]=1.[S:36](=[O:40])(=[O:39])([OH:38])[OH:37]>C(OCC)(=O)C>[S:36]([OH:40])([OH:39])(=[O:38])=[O:37].[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][C:25]([F:27])([F:26])[F:28])[CH:18]=3)=[CH:15][N:14]([C:29]3[CH:34]=[CH:33][C:32](=[O:35])[NH:31][N:30]=3)[N:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1118Sulfuric AcidHCID 10252096HCID 10252096, compound

Product 1

HCID 69416617HCID 69416617, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.5 ml of a dimethylsulfoxide solution containing 430 mg (1.00 mmol) of 3-(4-fluorophenyl)-1-(1,6-dihydro-6-oxopyridazin-3-yl)-4-[2-(2,2,2-trifluoroethyl)aminopyridin-4-yl]-1H-pyrazole obtained in Example 28-2) was added 0.2 ml of 0.041M dil. sulfuric acid at 45° C. over 5 minutes, and the mixture was stirred at the same temperature for 1 hour. Then, 3.0 ml of ethyl acetate was added to the mixture over 30 minutes, and the resulting mixture was further stirred for 5 minutes. Formed crystals were collected by filtration, washed with 100 ml of ethyl acetate, and dried under reduced pressure to obtain 464 mg of the title compound as a white powder. (Yield: 88%)

Workup

  1. stirringthe resulting mixture was further stirred for 5 minutes
  2. customFormed crystals
  3. filtrationwere collected by filtration
  4. washwashed with 100 ml of ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d716e177d1dc4b6a8db3eb97fd2feb96
Source dataset
uspto-grants-2007_11
Patent number
US07294625B2

Reaction notes

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