Potassium Carbonate → 2-{2-[(2-Isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethoxy}phenyl methanesulfonate

HRID 2422119Notes

Reaction equation

HRID 2422119 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][NH:14][C:15]2[C:16](=[O:31])[N:17]([CH:28]([CH3:30])[CH3:29])[S:18](=[O:27])(=[O:26])[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=O)=O)=CC=1.[CH3:32][S:33]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[OH:43])(=[O:35])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:32][S:33]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:43][CH2:12][CH2:13][NH:14][C:15]1[C:16](=[O:31])[N:17]([CH:28]([CH3:29])[CH3:30])[S:18](=[O:26])(=[O:27])[C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132483392-Hydroxyphenyl methanesulfonateHCID 866258832-[(2-Isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate

Product 1

HCID 866258822-{2-[(2-Isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethoxy}phenyl methanesulfonateYield 15%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

2-[(2-Isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate (200 mg, 0.431 mmol) was dissolved in dry MeCN (4 mL) under nitrogen atmosphere. 2-Hydroxyphenyl methanesulfonate (89 mg, 0.474 mmol) was added followed by potassium carbonate (297 mg, 2.152 mmol). The reaction mixture was heated in a microwave reactor for 15 mins at 120° C. Potassium carbonate was filtered off and the reaction mixture was concentrated and redissolved in EtOAc. The mixture was washed with NaHCO3, dried over Na2SO4, filtered and evaporated. The residue was purified on a Horizon™ flash system using Heptane and EtOAc as eluant and TEA as additative and then purified by column chromatography (ISOLUTE SI, (5 g)) using DCM as eluant to afford the title compound (31 mg, 15%). 1H NMR (CDCl3, 500 MHz): δ 1.59 (d, 6H), 3.22 (s, 3H), 3.31 (q, 2H), 3.96 (t, 2H), 4.38-4.46 (m, 1H), 5.88 (t, 1H), 6.89 (d, 1H), 7.02 (t, 1H), 7.23-7.30 (m, 2H), 7.46-7.48 (m, 3H), 7.53-7.56 (m, 2H); 13C NMR (CDCl3, 125 MHz): δ 20.38, 38.57, 43.36, 47.85, 67.23, 108.08, 114.71, 122.38, 124.59, 125.14, 128.55, 129.15, 130.09, 131.63, 135.62, 138.64, 150.55, 158.40; Mass Spectrum: M+H+ 481.1.

Workup

  1. filtrationPotassium carbonate was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionredissolved in EtOAc
  4. washThe mixture was washed with NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a Horizon™ flash system
  9. customTEA as additative and then purified by column chromatography (ISOLUTE SI, (5 g))

Sources & evidence

ORD record
ord-4fd7f60f369345c6a36f8ed9aaafcc51
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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