Potassium Carbonate → tert-butyl 4-[5-chloro-2-(2-chloro-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)phenyl]-1H-pyrazole-1-carboxylate

HRID 46351Notes

Reaction equation

HRID 46351 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=2)[CH:7]=1.[Cl:21][C:22]1[CH:23]=[C:24]([S:29]([N:32]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][C:40]=2[O:47][CH3:48])[C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1F.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cl-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][C:27]2[CH:26]=[CH:25][C:24]([S:29]([N:32]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][C:40]=3[O:47][CH3:48])[C:33]3[S:37][N:36]=[CH:35][N:34]=3)(=[O:30])=[O:31])=[CH:23][C:22]=2[Cl:21])=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH:12]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59436518tert-butyl 4-(5-chloro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylateHCID 594365343-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 59436520tert-butyl 4-[5-chloro-2-(2-chloro-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)phenyl]-1H-pyrazole-1-carboxylateYield 49.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 5234Sodium ChlorideSolvent

Procedure

tert-butyl 4-(5-chloro-2-hydroxyphenyl)-1H-pyrazole-1-carboxylate (Preparation 205, 99.6 mg, 0.338 mmol), 3-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 653, 153 mg, 0.345 mmol) and potassium carbonate (59.8 mg, 0.433 mmol) were stirred in dimethylsulphoxide (5 ml) at room temperature for 16 hours. The mixture was diluted with saturated aqueous sodium chloride solution (40 ml) and extracted with ethyl acetate (3×40 ml). The combined organics were dried over anhydrous magnesium sulphate, filtered and the solvents removed in vacuo to give the crude product which was purified by column chromatography using the ISCO® (using a gradient of 0-40% v/v ethyl acetate in heptane, 12 g SiO2) to give the title compound as a white solid (121 mg)

Workup

  1. extractionextracted with ethyl acetate (3×40 ml)
  2. dry with materialThe combined organics were dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customthe solvents removed in vacuo
  5. customto give the crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-aa20274950224244b39d95c98103c608
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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