Potassium Carbonate → HCID 58042271, compound

HRID 1619667Notes

Reaction equation

HRID 1619667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[N:17][CH:16]=3)[CH:9]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].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:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:21]([F:22])([F:24])[F:23])[CH:4]=3)=[CH:9][C:10]=2[C:15]2[CH:20]=[CH:19][N:18]=[N:17][CH:16]=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 136200883HCID 136200883, compound

Product 1

HCID 58042271HCID 58042271, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4′-Chloro-3-(pyridazin-4-yl)-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 56, 88 mg, 0.25 mmol) was dissolved in DMSO (1 mL), potassium carbonate (69 mg, 0.5 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 127 mg, 0.27 mmol). The reaction was stirred at room temperature for 3 hours and then partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was separated and washed with water (2×50 mL), dried over MgSO4, filtered and evaporated. The crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 20:80 to give the title compound (135 mg, 0.17 mmol, 69%) as a white solid.

Workup

  1. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  2. customThe organic phase was separated
  3. washwashed with water (2×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 20:80

Sources & evidence

ORD record
ord-ac6ad75347b44c11946c0cabdcec7de5
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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