Trifluoroacetic acid → 3-{[4-(4-Methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide

HRID 1526174ノート

反応式

HRID 1526174 の反応式
Cl[C:2]1[C:3]([C:22]([NH2:24])=[O:23])=[N:4][C:5]([C:18](O)([CH3:20])[CH3:19])=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:7]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.FC(F)(F)C(O)=O.CN1CCCC1=O>O>[CH3:25][N:26]1[CH2:27][CH2:28][N:29]([C:32]2[CH:38]=[CH:37][C:35]([NH:36][C:2]3[C:3]([C:22]([NH2:24])=[O:23])=[N:4][C:5]([C:18]([CH3:20])=[CH2:19])=[C:6]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=4)[N:7]=3)=[CH:34][CH:33]=2)[CH2:30][CH2:31]1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 13387N-methyl-2-pyrrolidoneHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 1176669023-Chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide

生成物 1

HCID 1176672673-{[4-(4-Methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide収率 56%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 3-chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (1.48 g), 4-(4-methylpiperazin-1-yl)aniline (883 mg), trifluoroacetic acid (385 μL), and N-methylpyrrolidone (14.8 mL) was heated to 160° C. for 5 hours. To the reaction mixture were added water and a saturated aqueous sodium hydrogen carbonate solution, and the precipitated solid was collected by filtration and then dried. The obtained solid was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-30:1:0.1) and washed with ethyl acetate to obtain 3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide (1.15 g) as an orange solid.

後処理

  1. filtrationa saturated aqueous sodium hydrogen carbonate solution, and the precipitated solid was collected by filtration
  2. customdried
  3. customThe obtained solid was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-30:1:0.1)
  4. washwashed with ethyl acetate

出典と根拠

ORDレコード
ord-0fcfb17e470d4b1c802ef4718dfb8600
出典データセット
uspto-grants-2015_07
特許番号
US09085540B2

反応ノート

読み込み中…