2-(Dimethyl-1,2-oxazol-4-yl)ethan-1-amine → 4-{[2-(3,5-Dimethylisoxazol-4-yl)ethyl]amino}-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2239729Notes

Reaction equation

HRID 2239729 reaction equation
Cl[C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][C:20]1[C:24]([CH2:25][CH2:26][NH2:27])=[C:23]([CH3:28])[O:22][N:21]=1>>[CH3:19][C:20]1[C:24]([CH2:25][CH2:26][NH:27][C:2]2[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:23]([CH3:28])[O:22][N:21]=1

Participants

3

Reactant 2

HCID 27585702-(Dimethyl-1,2-oxazol-4-yl)ethan-1-amineHCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 672444284-{[2-(3,5-Dimethylisoxazol-4-yl)ethyl]amino}-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Procedure

The title compound was prepared from 4-chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide and [2-(3,5-dimethylisoxazol-4-yl)ethyl]amine in a similar manner as described for Example 24. 1H NMR (500 MHz, CDCl3): δ 7.54-7.50 (m, 2H), 7.49-7.45 (m, 3H), 5.32 (t, 1H), 4.47 (sept, 1H), 3.04 (q, 2H), 2.33 (t, 2H), 2.14 (s, 3H), 2.01 (s, 3H), 1.59 (d, 6H); 13C NMR (125 MHz, CDCl3): δ 166.1, 159.4, 158.6, 134.9, 131.4, 130.2, 129.2, 125.1, 109.7, 107.9, 47.9, 43.3, 23.0, 20.4, 11.1, 10.2; Mass Spectrum: M+H+ 390

Sources & evidence

ORD record
ord-c9a89f145ac2472c8dc4ecabbd73f88b
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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