2-(4-hydroxyphenyl)-N,N-dimethylacetamide → 2-(4-{3-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propoxy}phenyl)-N,N-dimethylacetamide

HRID 2422026Notes

Reaction equation

HRID 2422026 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:4][CH:3]=1.CC1C=CC(S(O[CH2:25][CH2:26][CH2:27][NH:28][C:29]2[C:30](=[O:46])[N:31]([C:42]([CH3:45])([CH3:44])[CH3:43])[S:32](=[O:41])(=[O:40])[C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=O)=O)=CC=1>>[C:42]([N:31]1[C:30](=[O:46])[C:29]([NH:28][CH2:27][CH2:26][CH2:25][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:11]([CH3:12])[CH3:13])=[O:10])=[CH:6][CH:7]=2)=[C:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[S:32]1(=[O:40])=[O:41])([CH3:43])([CH3:44])[CH3:45]

Participants

3

Reactant 2

HCID 27738582-(4-hydroxyphenyl)-N,N-dimethylacetamideHCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate

Product 1

HCID 116274502-(4-{3-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propoxy}phenyl)-N,N-dimethylacetamideYield 59%

Procedure

The title compound was prepared as described for Example 12 from 2-(4-hydroxyphenyl)-N,N-dimethylacetamide and 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate. The reaction mixture was evaporated, purified twice by silica gel column chromatography (Horizons Biotage) using 75-85% EtOAc in petroleum ether 40-60° C. and then 50% DCM in EtOAc as eluent to give the title compound (0.072 g, 59%). 1H NMR (500 MHz CDCl3): δ 7.54-7.49 (m, 2H), 7.46-7.42 (m, 3H), 7.18 (d, 2H), 6.82 (d, 2H), 5.76 (t, 1H), 3.87 (t, 2H), 3.66 (s, 2H), 3.08 (m, 2H), 3.01 (s, 3H), 2.98 (s, 3H), 1.83 (m, 2H), 1.74 (s, 9H); 13C NMR (CDCl3): δ 171.5, 159.8, 157.4, 135.3, 131.8, 130.1, 129.7, 128.8, 127.8, 125.3, 114.8, 107.1, 66.1, 61.7, 42.5, 40.3, 37.9, 35.9, 28.9, 27.8; Mass Spectrum M+H+ 500.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was evaporated
  3. custompurified twice by silica gel column chromatography (Horizons Biotage)
  4. custom75-85% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-44eee43160c74a13996143a250241e9c
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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