4-(Pyrrolidin-1-yl)aniline → 2-tert-Butyl-5-phenyl-4-[(4-pyrrolidin-1-ylphenyl)amino]isothiazol-3(2H)-one 1,1-dioxide

HRID 729284Notes

Reaction equation

HRID 729284 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[N:20]1([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1>CC#N.CN(C=O)C>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:30][CH:29]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8088414-(Pyrrolidin-1-yl)anilineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 115754672-tert-Butyl-5-phenyl-4-[(4-pyrrolidin-1-ylphenyl)amino]isothiazol-3(2H)-one 1,1-dioxideYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.500 mmol), (4-pyrrolidin-1-ylphenyl)amine (0.081 g, 0.500 mmol) and TEA (0.070 ml, 0.500 mmol) in MeCN (2 ml) and DMF (1 ml) was heated in a microwave reactor at 120° C. for 45 mins. TEA (0.070 ml, 0.500 mmol) was added and the mixture was heated at 120° C. for 15 mins. The precipitate from the reaction mixture was isolated by filtration and washed with MeCN. The crude product was dissolved in MeOH and purified by silica gel column chromatography using 15-100% EtOAc in petroleum ether 40-60° C. as eluent, to give the title compound (0.146 g, 69%). 1H NMR (500 MHz, CDCl3): δ 7.22-7.02 (m, 5H), 6.55 (d, 2H), 6.14 (d, 2H), 3.15-3.10 (m, 4H), 1.99-1.92 (m, 4H), 1.77 (s, 9H); 13C NMR (125 MHz CDCl3): δ 160.8, 149.9, 131.6, 129.7, 128.5, 127.9, 125.5, 124.7, 123.9, 111.2, 108.8, 61.8, 47.9, 27.9, 25.6; Mass Spectrum: M+H+ 426.

Workup

  1. temperaturethe mixture was heated at 120° C. for 15 mins
  2. customThe precipitate from the reaction mixture was isolated by filtration
  3. washwashed with MeCN
  4. dissolutionThe crude product was dissolved in MeOH
  5. custompurified by silica gel column chromatography
  6. custom15-100% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-c44ac96ba20743bbac0a5708cab756f9
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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