Methanesulfonyl chloride → HCID 131723416, compound

HRID 1167551Notes

Reaction equation

HRID 1167551 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-a642fb81d6cc47788e5b632c098ffce6
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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