Potassium Carbonate → tert-Butyl 3-{5-[2-(2-cyano-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)-5-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}azetidine-1-carboxylate

HRID 46396Notes

Reaction equation

HRID 46396 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]1[N:16]([CH:17]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[N:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]([C:36]1[CH:37]=[C:38]([S:43]([N:46]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][C:54]=2[O:61][CH3:62])[C:47]2[S:51][N:50]=[CH:49][N:48]=2)(=[O:45])=[O:44])[CH:39]=[CH:40][C:41]=1F)#[N:35]>CS(C)=O>[C:34]([C:36]1[CH:37]=[C:38]([S:43]([N:46]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][C:54]=2[O:61][CH3:62])[C:47]2[S:51][N:50]=[CH:49][N:48]=2)(=[O:45])=[O:44])[CH:39]=[CH:40][C:41]=1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[C:12]1[N:16]([CH:17]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[N:15]=[CH:14][CH:13]=1)#[N:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 136063628tert-Butyl 3-[5-(5-trifluoromethyl-2-hydroxyphenyl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

Product 1

HCID 59436615tert-Butyl 3-{5-[2-(2-cyano-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)-5-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

tert-Butyl 3-{5-[2-hydroxy-5-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}azetidine-1-carboxylate, (Preparation 883, 2.20 g, 0.00574 mol), potassium carbonate (1.60 g, 0.0116 mol) and 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide, (Preparation 68, 2.50 g, 0.00575 mol) were combined in a 50 mL round bottomed flask and the flask was cooled in ice. Dimethylsulphoxide (15 mL) was added and after a few minutes the ice bath was removed and the reaction was stirred at room temperature for 3 hours under nitrogen. The reaction was diluted with water (50 mL) and extracted with tert-butylmethylether (100 mL) and the organic layer was washed with water (30 mL). The organic extracts were dried over anhydrous sodium sulphate, filtered and the solvent removed in vacuo to give the title compound as a white foam (4.76 g).

Workup

  1. customwere combined in a 50 mL round bottomed flask
  2. temperaturethe flask was cooled in ice
  3. customwas removed
  4. additionThe reaction was diluted with water (50 mL)
  5. extractionextracted with tert-butylmethylether (100 mL)
  6. washthe organic layer was washed with water (30 mL)
  7. dry with materialThe organic extracts were dried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c61f010642104f76a493188369aa46a1
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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