Dimethyl Sulfoxide → HCID 86604014, compound

HRID 1592921Notes

Reaction equation

HRID 1592921 reaction equation
CS(C)=O.[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[N:14][N:15]([C:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][N:18]=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1.O.[C:32]1([S:38]([OH:41])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(OCC)(=O)C>[C:32]1([S:38]([OH:41])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[N:14][N:15]([C:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][N:18]=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 10043323HCID 10043323, compoundHCID 15619088Hydroxybenzenesulfonic acid

Product 1

HCID 86604014HCID 86604014, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.5 ml of a dimethylsulfoxide solution containing 174 mg (0.50 mmol) of 4-(2-aminopyridin-4-yl)-3-(4-fluorophenyl)-1-(1,6-dihydro-6-oxopyridazin-3-yl)-1H-pyrazole obtained by the same reaction as in Example 2-4) was added 0.3 ml of a dimethylsulfoxide solution containing 185 mg (1.05 mmol) of benzenesulfonic acid monohydrate at 45° C. over 15 minutes, and the mixture was stirred at the same temperature for 30 minutes. Then, 17 ml of ethyl acetate was added to the mixture over 10 minutes, and after gradually cooling the mixture to room temperature, the mixture was further stirred for 30 minutes. Formed crystals were collected by filtration, washed with 20 ml of ethyl acetate, and dried under reduced pressure to obtain 210 mg of the title compound as a white powder. (Yield: 83%)

Workup

  1. customobtained by the same reaction as in Example 2-4)
  2. stirringthe mixture was further stirred for 30 minutes
  3. customFormed crystals
  4. filtrationwere collected by filtration
  5. washwashed with 20 ml of ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-3bed926c8ba84f658041fc2dd6ee76b8
Source dataset
uspto-grants-2007_11
Patent number
US07294625B2

Reaction notes

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