Water → HCID 15020538, compound

HRID 1461829Notes

Reaction equation

HRID 1461829 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[N:9]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[N:34]#CBr.O>CS(C)=O>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[N:9]=[C:8]2[N:5]1[CH2:4][CH2:3][N:2]([C:1]#[N:34])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 148234483-(4-methyl-1-piperazinyl)-5-methoxy-1-phenylsulfonyl-1H-indazole

Product 1

HCID 15020538HCID 15020538, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 3-(4-methyl-1-piperazinyl)-5-methoxy-1-phenylsulfonyl-1H-indazole (55.0 g, 0.14 mol) of Example 5d, potassium carbonate (22.0 g, 0.16 mol) and dimethylsulfoxide (DMSO) [500 ml] under N2 was added dropwise, cyanogen bromide (16.0 g, 0.15 mol) dissolved in DMSO (125 ml). The reaction was stirred at room temperature for 4 hours and was then poured into H2O (2.5 l). The solid which formed was collected and washed well with H2O. The solid was dried and weighed to yield 41.0 g. A 5.0 g sample was recrystallized twice from ethanol (utilizing decolorizing carbon) to afford 3.5 g (50%) of 4-(5-methoxy-1-phenylsulfonyl-1H-indazol-3-yl)-1-piperazinecarbonitrile. m.p. 171°-173° C.

Workup

  1. additionwas added dropwise
  2. customThe solid which formed
  3. customwas collected
  4. washwashed well with H2O
  5. customThe solid was dried
  6. customto yield 41.0 g
  7. customA 5.0 g sample was recrystallized twice from ethanol (utilizing decolorizing carbon)

Sources & evidence

ORD record
ord-8543daf264ad4ae792e40819a2a0247b
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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