Potassium Carbonate → 4-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide

HRID 46231Notes

Reaction equation

HRID 46231 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:8]2[CH:7]=[CH:6][C:5]([S:10]([NH:13][C:14]3[S:15][CH:16]=[CH:17][N:18]=3)(=[O:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])=[C:22]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422683-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamideHCID 1355532144-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol

Product 1

HCID 594365994-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyano-4-fluoro-N-1,3-thiazol-2-ylbenzenesulfonamide, (Preparation 46, 500 mg, 0.00176 mol), 4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol, (Preparation 89, 370 mg, 0.00177 mol) and potassium carbonate (700 mg, 0.00287 mol) were stirred in dimethylformamide (5 mL) at 80° C. for 24 hours. The reaction mixture was cooled and partitioned between ethyl acetate (150 mL) and aqueous hydrochloric acid (80 mL of 2 molar), the organic layer was dried over anhydrous sodium sulphate, filtered and the solvents removed in vacuo to give an orange solid. The solid was triturated with diethyl ether (20 mL) to give the title compound as an orange powder, (680 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate (150 mL) and aqueous hydrochloric acid (80 mL of 2 molar)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customthe solvents removed in vacuo
  6. customto give an orange solid
  7. customThe solid was triturated with diethyl ether (20 mL)

Sources & evidence

ORD record
ord-b86942f9b1814e209562758257dd6bb3
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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