Benzenamine, 4-(4-morpholinyl)- → HCID 11546409, compound

HRID 729289Notes

Reaction equation

HRID 729289 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.[N:19]1([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CC#N>[CH:15]([N:4]1[C:3](=[O:18])[C:2]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:30][CH:29]=2)=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:5]1(=[O:14])=[O:13])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11546409HCID 11546409, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.525 mmol), (4-morpholin-4-ylphenyl)amine (0.094 g, 0.525 mmol) and TEA (0.070 ml, 0.525 mmol) in MeCN (2 ml) was heated in a microwave reactor at 150° C. for 15 mins and 160° C. for 30 mins. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography using 35% EtOAc in hexane as eluent, to give the title compound (0.157 g, 70%). 1H NMR (500 MHz CDCl3): δ 7.24-7.18 (m, 1H), 7.15-7.10 (m, 5H), 6.64 (d, 2H), 6.59 (bs, 2H), 4.54-4.45 (m 1H), 3.85 (bs, 4H), 3.03 (bs, 4H), 1.65 (d, 6H); 13C NMR (125 MHz CDCl3): δ 159.1, 131.3, 129.5, 128.9, 128.2, 125.2, 123.6, 15.9, 66.8, 50.0, 47.9, 20.5; Mass spectrum: M+H+ 428.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf768899d9cf48cca62074e2ef0c7b77
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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