5-cyclohexyl-2-methoxyaniline → 4-[(5-cyclohexyl-2-methoxyphenyl)amino]-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729318Notes

Reaction equation

HRID 729318 reaction equation
Cl[C:2]1[C:3](=[O:19])[N:4]([CH2:15][CH2:16][O:17][CH3:18])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:20]1([C:26]2[CH:27]=[CH:28][C:29]([O:33][CH3:34])=[C:30]([CH:32]=2)[NH2:31])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH:20]1([C:26]2[CH:27]=[CH:28][C:29]([O:33][CH3:34])=[C:30]([NH:31][C:2]3[C:3](=[O:19])[N:4]([CH2:15][CH2:16][O:17][CH3:18])[S:5](=[O:14])(=[O:13])[C:6]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:32]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 27579915-cyclohexyl-2-methoxyanilineHCID 672439094-Chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 114964874-[(5-cyclohexyl-2-methoxyphenyl)amino]-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Procedure

The title compound was prepared from 4-chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 5-cyclohexyl-2-methoxyaniline in a similar manner as described for Examples 9 and 13. 1H NMR (400 MHz, CD3CN): δ 0.92-1.05 (m, 2H), 1.08-1.33 (m, 3H), 1.41-1.49 (m, 2H), 1.62-1.76 (m, 3H), 2.05-2.15 (m, 1H), 3.38 (s, 3H), 3.70-3.75 (m, 5H), 3.91 (t, 2H), 6.41 (d, 1H), 6.70 (d, 1H), 6.79-6.83 (m, 1H), 7.12-7.22 (m, 4H), 7.24-7.30 (m, 1H), 7.55 (bs, 1H); Mass Spectrum: M+H+ 471.

Sources & evidence

ORD record
ord-c559f3e6c2244bfcb478b62577e4b329
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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