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

HRID 2290657ノート

反応式

HRID 2290657 の反応式
[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

参加物

6

反応物 3

HCID 7912Diisopropylamine3 回HCID 98211042,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-amineHCID 123682034-Iodo-1-phthalimido-pentane3 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-dae485710f714fd2b1eabc4ca236d563
出典データセット
uspto-grants-1986_10
特許番号
US04617394

反応ノート

読み込み中…