Potassium Carbonate → HCID 58042252, compound

HRID 1619663Notes

Reaction equation

HRID 1619663 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[N:11][CH:10]=2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[C:33](F)=[CH:34][C:35]([F:58])=[C:36]([S:38]([N:41]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=2[O:56][CH3:57])[C:42]2[S:43][CH:44]=[N:45][N:46]=2)(=[O:40])=[O:39])[CH:37]=1>CS(C)=O>[Cl:31][C:32]1[C:33]([O:8][C:6]2[C:5]([C:9]3[CH:14]=[CH:13][N:12]=[N:11][CH:10]=3)=[CH:4][C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=3)=[C:2]([Cl:1])[CH:7]=2)=[CH:34][C:35]([F:58])=[C:36]([S:38]([N:41]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=2[O:56][CH3:57])[C:42]2[S:43][CH:44]=[N:45][N:46]=2)(=[O:39])=[O:40])[CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 136200885HCID 136200885, compound

Product 1

HCID 58042252HCID 58042252, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Chloro-5-(pyridazin-4-yl)-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 52, 140 mg, 0.4 mmol) was dissolved in DMSO (1 mL) and potassium carbonate (110 mg, 0.8 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 203 mg, 0.44 mmol). The reaction was stirred at room temperature for 18 hours and then partitioned between ethyl acetate (50 mL) and water (40 mL). The ethyl acetate was separated and dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 80:20 to 20:80 to give the title compound (231 mg, 0.30 mmol, 73%) as a white solid.

Workup

  1. custompartitioned between ethyl acetate (50 mL) and water (40 mL)
  2. customThe ethyl acetate was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 80:20 to 20:80

Sources & evidence

ORD record
ord-5d3133ef438943919b81db5d51592ef1
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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