Potassium Carbonate → 3-Chloro-4-[(3-pyridazin-4-ylbiphenyl-4-yl)oxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619592Notes

Reaction equation

HRID 1619592 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:12]=2[OH:13])=[CH:3][N:2]=1.[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([N:31](CC2C=CC(OC)=CC=2OC)[C:32]2[S:33][CH:34]=[N:35][N:36]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1F.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([NH:31][C:32]2[S:33][CH:34]=[N:35][N:36]=2)(=[O:29])=[O:30])[CH:24]=[CH:25][C:26]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422903-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideHCID 1362008863-Pyridazin-4-ylbiphenyl-4-ol

Product 1

HCID 566007903-Chloro-4-[(3-pyridazin-4-ylbiphenyl-4-yl)oxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Pyridazin-4-ylbiphenyl-4-ol (Preparation 4, 40 mg, 0.16 mmol) and 3-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 17, 72 mg, 0.16 mmol) were dissolved in dimethylsulfoxide (2 mL). Potassium carbonate (67 mg, 0.5 mmol) was added and the reaction stirred at room temperature for 16 hours. The crude material was partitioned between ethyl acetate (20 mL) and water (20 mL), the organic layer separated, concentrated in vacuo, dissolved in trifluoroacetic acid (1 mL) and the solution stirred for 16 hours at room temperature. The reaction was then concentrated in vacuo and purified by silica gel column chromatography (ISCO™, 12 g silica, 50-100% ethyl acetate in heptane gradient elution). The appropriate fractions were combined and concentrated in vacuo to afford the title compound as a white solid (41 mg, 49%).

Workup

  1. customThe crude material was partitioned between ethyl acetate (20 mL) and water (20 mL)
  2. customthe organic layer separated
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in trifluoroacetic acid (1 mL)
  5. stirringthe solution stirred for 16 hours at room temperature
  6. concentrationThe reaction was then concentrated in vacuo
  7. custompurified by silica gel column chromatography (ISCO™, 12 g silica, 50-100% ethyl acetate in heptane gradient elution)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b00a45166bc44c28630109aae7411d3
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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