Potassium Carbonate → 3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-2'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 1619637Notes

Reaction equation

HRID 1619637 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:14]2[S:18][N:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[N:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[C:38]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[C:49]([F:52])([F:51])[F:50])[CH:39]=[CH:40][C:41]=2[OH:42])=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:14]2[S:18][N:17]=[CH:16][N:15]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][C:8]=1[O:42][C:41]1[CH:40]=[CH:39][C:38]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:49]([F:50])([F:51])[F:52])=[CH:37][C:36]=1[C:33]1[CH:34]=[CH:35][N:30]=[N:31][CH:32]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 136200882HCID 136200882, compound

Product 1

HCID 580422833-Cyano-N-(2,4-dimethoxybenzyl)-4-{[3-pyridazin-4-yl-2'-(trifluoromethyl)biphenyl-4-yl]oxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamideYield 115.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 19, 206 mg, 0.474 mmol) and 3-pyridazin-4-yl-2′-(trifluoromethyl)biphenyl-4-ol (Preparation 9, 150 mg, 0.474 mmol) in dimethylsulfoxide (5 mL) was added potassium carbonate (196 mg, 1.42 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with a 1M aqueous solution of sodium hydroxide whereupon a precipitate formed. The precipitate was collected by filtration and washed with water to afford the title compound as a solid (400 mg, 115%, contains residual dimethylsulfoxide). The material was used without purification in the next step.

Workup

  1. customThe reaction mixture was quenched with a 1M aqueous solution of sodium hydroxide whereupon a precipitate
  2. customformed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-44eaac5644b5459ea9786219c91804e7
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…