3-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate → HCID 11582415, compound

HRID 2239630Notes

Reaction equation

HRID 2239630 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CC1C=CC(S(O[CH2:19][CH2:20][CH2:21][NH:22][C:23]2[C:24](=[O:40])[N:25]([C:36]([CH3:39])([CH3:38])[CH3:37])[S:26](=[O:35])(=[O:34])[C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=O)=O)=CC=1>CCOC(C)=O>[C:36]([N:25]1[C:24](=[O:40])[C:23]([NH:22][CH2:21][CH2:20][CH2:19][O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[C:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[S:26]1(=[O:34])=[O:35])([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonateHCID 178418642HCID 178418642, compound

Product 1

HCID 11582415HCID 11582415, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared as described for Example 12 from 4-hydroxypyridine and 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate with a reaction time of 15 mins. EtOAc was added to the reaction mixture and the mixture was washed with water, brine and evaporated. The residue was purified twice by silica gel column chromatography (Horizons Biotage) using 50-80% EtOAc in hexane then 50% EtOAc in DCM as eluent to give the title compound (0.035 g, 35%). 1H NMR (500 MHz CDCl3): δ 8.44 (d, 2H), 7.54-7.48 (m, 2H), 7.48-7.41 (m, 3H), 6.75 (d, 2H), 5.64 (t, 1H), 3.91 (t, 2H), 3.114-3.08 (m, 2H), 1.90-1.82 (m, 2H), 1.74 (s, 9H); 13C NMR (125 MHz CDCl3): δ 164.5, 159.8, 151.4, 135.2, 131.8, 129.9, 128.9, 125.2, 110.3, 107.6, 65.7, 61.8, 41.9, 28.8, 27.9; Mass Spectrum: M+H+ 416.

Workup

  1. customThe title compound was prepared
  2. washthe mixture was washed with water, brine
  3. customevaporated
  4. customThe residue was purified twice by silica gel column chromatography (Horizons Biotage)

Sources & evidence

ORD record
ord-ecc9d5985728447ea2a557cc398862fd
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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