Dimethyl Sulfoxide → HCID 86604015, compound

HRID 1592923Notes

Reaction equation

HRID 1592923 reaction equation
CS(C)=O.[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:14][N:15]([C:17]3[CH:18]=[CH:19][C:20]4[N:21]([CH:23]=[N:24][N:25]=4)[N:22]=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1.[CH3:33][S:34]([OH:37])(=[O:36])=[O:35]>C(OCC)(=O)C>[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[C:13]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:14][N:15]([C:17]3[CH:18]=[CH:19][C:20]4[N:21]([CH:23]=[N:24][N:25]=4)[N:22]=3)[CH:16]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 6395Methanesulfonic AcidHCID 9976519HCID 9976519, compound

Product 1

HCID 86604015HCID 86604015, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 50 ml of a dimethylsulfoxide solution containing 5.00 g (13.4 mmol) of 4-(2-aminopyridin-4-yl)-3-(4-fluorophenyl)-1-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazole obtained by the same reaction as in Example 8-2) was added 2.35 ml (36.2 mmol) of methanesulfonic acid at 50° C. over 15 minutes, and the mixture was stirred at the same temperature for 1 hour. Then, 100 ml of ethyl acetate was added to the mixture over 10 minutes, and the resulting mixture was further stirred for 1 hour. Formed crystals were collected by filtration, washed with 150 ml of ethyl acetate, and dried under reduced pressure to obtain 5.80 g of the title compound as a beige powder. (Yield: 92%)

Workup

  1. customobtained by the same reaction as in Example 8-2)
  2. stirringthe resulting mixture was further stirred for 1 hour
  3. customFormed crystals
  4. filtrationwere collected by filtration
  5. washwashed with 150 ml of ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ac5a6b2473114f4392389728072addb7
Source dataset
uspto-grants-2007_11
Patent number
US07294625B2

Reaction notes

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