Methanesulfonyl chloride → HCID 131723416, compound

HRID 489958Notes

Reaction equation

HRID 489958 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-a53bdf209d154ac5a8449540b4856f26
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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