Water → 4-Chloro-N-{5-chloro-2-[2-(2-hydroxy-ethoxy)-pyridine-4-carbonyl]-pyridin-3-yl}-3-trifluoromethyl-benzenesulfonamide

HRID 419152Notes

Reaction equation

HRID 419152 reaction equation
C([Si](C)(C)OCC[C:9]1[CH:14]=[C:13]([C:15]([C:17]2[C:22]([N:23](COC)[S:24]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=3)(=[O:26])=[O:25])=[CH:21][C:20]([Cl:41])=[CH:19][N:18]=2)=[O:16])[CH:12]=[CH:11][N:10]=1)(C)(C)C.O.[O:45]1CC[O:48][CH2:47][CH2:46]1>Cl>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([NH:23][C:22]2[C:17]([C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([O:45][CH2:46][CH2:47][OH:48])[CH:14]=3)=[O:16])=[N:18][CH:19]=[C:20]([Cl:41])[CH:21]=2)(=[O:25])=[O:26])=[CH:28][C:29]=1[C:34]([F:37])([F:36])[F:35]

Participants

5

Reactant 3

HCID 962WaterHCID 312751,4-DioxaneHCID 57942209N-(2-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridine-4-carbonyl}-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579424454-Chloro-N-{5-chloro-2-[2-(2-hydroxy-ethoxy)-pyridine-4-carbonyl]-pyridin-3-yl}-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(2-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridine-4-carbonyl}-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide in 4N HCl in dioxane (4 mL) and water (1 mL) was stirred at 100° C. for overnight. The reaction mixture was cooled to room temperature, evaporated to dryness and treated with saturated aqueous NaHCO3 solution till pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The crude product was purified by HPLC. 1H NMR (400 MHz, CDCl3) δ 10.82 (s, 1H), 8.35 (m, 1H), 8.24 (m, 1H), 8.15-8.18 (m, 2H), 7.96 (m, 1H), 7.63 (m, 1H), 7.17 (m, 1H), 7.09 (m, 1H), 4.51 (m, 2H), 3.97 (m, 2H), 3.09 (m, 1H); MS: (M+H)/z=535.9.

Workup

  1. customevaporated to dryness
  2. additiontreated with saturated aqueous NaHCO3 solution till pH 7-8
  3. extractionThe mixture was extracted with EtOAc (2×25 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-5a4a3aadebe34f409193ffe31aa9d590
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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