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

HRID 2422031Notes

Reaction equation

HRID 2422031 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-c09ea1621827465fb4cf9cc6f16bde1e
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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