Diisopropylamine → 2-(4-((2,6-Dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)amino)pentyl)isoindoline-1,3-dione

HRID 2290657노트

반응식

HRID 2290657 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([O:26][CH3:27])[C:5]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[C:7]2[CH3:14].C(NC(C)C)(C)C.I[CH:36]([CH3:51])[CH2:37][CH2:38][CH2:39][N:40]1[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]2[C:41]1=[O:50]>CC#N.O>[CH3:13][O:12][C:9]1[CH:8]=[C:7]([CH3:14])[C:6]2[C:11](=[C:2]([NH:1][CH:36]([CH3:51])[CH2:37][CH2:38][CH2:39][N:40]3[C:44](=[O:45])[C:43]4=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]4[C:41]3=[O:50])[CH:3]=[C:4]([O:26][CH3:27])[C:5]=2[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[N:10]=1

참가 물질

6

반응물 3

HCID 7912Diisopropylamine3회HCID 98211042,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-amineHCID 123682034-Iodo-1-phthalimido-pentane3회

생성물 1

HCID 137459272-(4-((2,6-Dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)amino)pentyl)isoindoline-1,3-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 8-amino-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline (8.0 g, 21.2 mmol), diisopropylamine (2.14 g, 21.2 mmol) and 4-iodo-1-phthalimidopentane (IPP) (7.26 g, 21.2 mmol) in CH3CN (40 mL) was refluxed for 24 hours after which time additional diisopropylamine (2.14 g, 21.2 mmol) and IPP (7.26 g, 21.2 mmol) were added. After refluxing a further 24 hours, more diisopropylamine (1.07 g, 10.6 mmol) and IPP (3.63 g, 10.6 mmol) were added and refluxing was continued a further 24 hours. The cooled mixture was diluted with H2O (20 mL) and stirred in an ice bath until crystallization was complete. Filtration and recrystallization from IPA gave 8.4 g (67%) of 1st crop title compound, mp 120°-124° C. Further recrystallization raised the mp to 121°-124° C.

후처리

  1. additionwere added
  2. temperatureAfter refluxing a further 24 hours
  3. temperaturerefluxing
  4. filtrationFiltration and recrystallization from IPA

출처 및 근거

ORD 기록
ord-dae485710f714fd2b1eabc4ca236d563
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04617394

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