Potassium Carbonate → HCID 58042265, compound

HRID 1619655Notes

Reaction equation

HRID 1619655 reaction equation
[CH3:1][N:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[CH:10]=[CH:11][C:12]=1[OH:13])=[O:6].[Cl:25][C:26]1[C:27](F)=[CH:28][C:29]([F:52])=[C:30]([S:32]([N:35]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=2[O:50][CH3:51])[C:36]2[S:37][CH:38]=[N:39][N:40]=2)(=[O:34])=[O:33])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O>[Cl:25][C:26]1[C:27]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]([F:22])([F:21])[F:23])=[CH:8][C:7]=2[C:5](=[O:6])/[CH:4]=[CH:3]/[N:2]([CH3:1])[CH3:24])=[CH:28][C:29]([F:52])=[C:30]([S:32]([N:35]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=2[O:50][CH3:51])[C:36]2[S:37][CH:38]=[N:39][N:40]=2)(=[O:33])=[O:34])[CH:31]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 58042330HCID 58042330, compound

Product 1

HCID 58042265HCID 58042265, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of (2E)-3-(Dimethylamino)-1-[4-hydroxy-2′-(trifluoromethyl)biphenyl-3-yl]prop-2-en-1-one (Preparation 43, 809 mg, 2.41 mmol) and 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 16, 1.10 g, 2.39 mmol) in dimethylsulfoxide (10.0 mL) was added potassium carbonate (859 mg, 6.22 mmol). The reaction mixture was stirred for 18 hours at room temperature under an atmosphere of nitrogen. The reaction was poured into a saturated solution of aqueous ammonium chloride (20 mL) and extracted with dichloromethane (3×40 mL). The combined organic phase was washed with brine (3×40 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow solid (1.96 g). The solid was purified by silica gel column chromatography (40%-75% ethyl acetate in heptane gradient elution) to afford the title compound as a clear glass (563 mg, 30%)

Workup

  1. extractionextracted with dichloromethane (3×40 mL)
  2. washThe combined organic phase was washed with brine (3×40 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db6148edea214c268223d12f34d83cdf
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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