Potassium Carbonate → 4-{4-Chloro-2-[2-(cyclobutyloxy)pyridin-4-yl]phenoxy}-3-cyano-N-(2,4-dimethoxybenzyl)-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46382Notes

Reaction equation

HRID 46382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH:16]3[CH2:19][CH2:18][CH2:17]3)[CH:10]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:26]([C:28]1[CH:29]=[C:30]([S:35]([N:38]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=2[O:53][CH3:54])[C:39]2[S:43][N:42]=[CH:41][N:40]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1F)#[N:27]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:33]2[CH:32]=[CH:31][C:30]([S:35]([N:38]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=3[O:53][CH3:54])[C:39]3[S:43][N:42]=[CH:41][N:40]=3)(=[O:37])=[O:36])=[CH:29][C:28]=2[C:26]#[N:27])=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH:16]3[CH2:19][CH2:18][CH2:17]3)[CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 1360636164-Chloro-2-[2-(cyclobutyloxy)pyridin-4-yl]phenol

Product 1

HCID 594365604-{4-Chloro-2-[2-(cyclobutyloxy)pyridin-4-yl]phenoxy}-3-cyano-N-(2,4-dimethoxybenzyl)-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Chloro-2-[2-(cyclobutyloxy)pyridin-4-yl]phenol, (Preparation 862, 20.5 mg, 0.000074 mol) was dissolved in dimethylsulphoxide (1 mL). Potassium carbonate (24.6 mg, 0.00018 mol) was added and the reaction stirred for 10 minutes at room temperature. 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide, (Preparation 68, 32.2 mg, 0.000074 mol) was added and the reaction was stirred at room temperature for 15 hours under nitrogen. The reaction was partitioned between a saturated aqueous sodium chloride solution (10 mL) and ethyl acetate (10 mL), the organic layer was washed with water (30 mL). The organic extracts were dried over anhydrous magnesium sulphate, filtered and the solvent removed in vacuo to give a colourless foam (56 mg). The material was purified using an ISCO™ companion (4 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a colourless oil (45 mg).

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 15 hours under nitrogen
  3. customThe reaction was partitioned between a saturated aqueous sodium chloride solution (10 mL) and ethyl acetate (10 mL)
  4. washthe organic layer was washed with water (30 mL)
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-61b1c1bf792a4be6bb6eba33d69eb8f1
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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