Benzenamine, 4-(hexahydro-1H-azepin-1-yl)- → 4-[(4-Azepan-1-ylphenyl)amino]-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729288

반응식

HRID 729288 반응식
[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:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CC#N>[N:20]1([C:27]2[CH:28]=[CH:29][C:30]([NH:33][C:8]3[C:9](=[O:10])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6](=[O:19])(=[O:18])[C:7]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:31][CH:32]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

참가 물질

4

반응물 2

HCID 93643Benzenamine, 4-(hexahydro-1H-azepin-1-yl)-HCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

생성물 1

HCID 116553914-[(4-Azepan-1-ylphenyl)amino]-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide수율 53.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

A mixture of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.500 mmol), (4-azepan-1-ylphenyl)amine (0.095 g, 0.500 mmol) and TEA (0.070 ml, 0.500 mmol) in MeCN (2 ml) was heated in a microwave reactor at 120° C. for 65 mins. TEA (0.070 ml, 0.500 mol) was added and the reaction mixture was heated in a microwave reactor at 120° C. for 15 mins. The reaction mixture was filtered and the residue was purified by silica gel column chromatography using 15-20% EtOAc in petroleum ether 40-60° C. as eluent, to give the title compound (0.121 g, 53%). 1H NMR (500 MHz CDCl3): δ 7.16-7.04 (m, 5H), 7.00 (s, 1H), 6.53 (d, 2H), 6.23 (d, 2H), 3.33 (t, 4H), 1.77 (s, 9H), 1.73-1.61 (m, 4H), 1.50-1.45 (m, 4H); 13C NMR (125 MHz CDCl3): δ 160.4, 146.6, 131.8, 129.8, 128.5, 127.9, 125.4, 124.5, 124.3, 110.7, 108.3, 61.8, 49.7, 27.9, 27.3, 26.9; Mass Spectrum: M+H+ 454.

후처리

  1. temperaturethe reaction mixture was heated in a microwave reactor at 120° C. for 15 mins
  2. filtrationThe reaction mixture was filtered
  3. customthe residue was purified by silica gel column chromatography
  4. custom15-20% EtOAc in petroleum ether 40-60° C.

출처 및 근거

ORD 기록
ord-fb2635a947b04f7faf6728b41262a14a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582629B2

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