Methanesulfonyl chloride → HCID 131723416, compound

HRID 1060948Notes

Reaction equation

HRID 1060948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[OH2:27].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][N:10]=[C:11]([N:19]3[CH2:20][CH2:21][N:22]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:23][CH2:24]3)[C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178478002HCID 178478002, compound

Product 1

HCID 131723416HCID 131723416, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperazinyl)pyrazole (200 mg; 0.54 mmol; prepared as set forth in Example A-169), methanesulfonyl chloride (75 mg) and 4-dimethylaminopyridine (5 mg) in pyridine was stirred at room temperature for 3 hours. The solvent was removed in vacuo and the residue was treated with water. The resultant crystalline solid was filtered, air dried and recrystallized from methanol and water to give 118 mg (37%) of 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-4-(methylsulfonyl)piperazine, monohydrate, m.p. 245-248° C. Anal. Calc'd. for C19H20ClN5SO2.H2O: C, 52.35; H, 5.09; N, 16.07. Found: C, 52.18; H, 5.31; N, 16.00.

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water
  4. filtrationThe resultant crystalline solid was filtered
  5. customair dried
  6. customrecrystallized from methanol and water

Sources & evidence

ORD record
ord-fc2baf9c1c9a4e17bd2fe071074d657f
Source dataset
uspto-grants-2003_02
Patent number
US06525059B1

Reaction notes

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