5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride → HCID 54427057, compound

HRID 1249700Notes

Reaction equation

HRID 1249700 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5].[Cl:27][C:28]1[N:32]([CH3:33])[N:31]=[C:30]([CH3:34])[C:29]=1[S:35](Cl)(=[O:37])=[O:36]>N1C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:2]([NH:1][S:35]([C:29]2[C:30]([CH3:34])=[N:31][N:32]([CH3:33])[C:28]=2[Cl:27])(=[O:36])=[O:37])=[C:3]([CH:22]=1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 27771265-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 22495876HCID 22495876, compound

Product 1

HCID 54427057HCID 54427057, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

250 mg (0.60 mmol) of 2-amino-5-chloro-N-(4-(thiomorpholine-4-sulfonyl)-phenyl)-benzamide were dissolved in 10 ml of dry pyridine, and a solution of 195 mg (0.85 mmol) 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride in 5 ml of pyridine was added dropwise at 0° C. After 2 h the mixture was poured onto ice, the precipitated solid was filtered off with suction and purified by chromatography over silica with methylene chloride/methanol (98:2). 250 mg (69%) of the title compound having a melting point of 215-216° C. were obtained.

Workup

  1. additionAfter 2 h the mixture was poured onto ice
  2. filtrationthe precipitated solid was filtered off with suction
  3. custompurified by chromatography over silica with methylene chloride/methanol (98:2)
  4. customwere obtained

Sources & evidence

ORD record
ord-595e600d509f49919a3bfbf182cee7b9
Source dataset
uspto-grants-2002_01
Patent number
US06335334B1

Reaction notes

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