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N-methyl-2-pyrrolidone → tert-butyl (3R)-3-{[5-carbamoyl-6-({-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-3-(prop-1-en-2-yl)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate

HRID 1526191
ノート
印刷プレビュー

反応式

HRID 1526191 の反応式
[C:1]([C:4]1[N:5]=[C:6]([C:24](O)([CH3:26])[CH3:25])[C:7]([O:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:8][C:9]=1Cl)(=[O:3])[NH2:2].[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH:35]2[CH2:40][CH2:39][N:38]([C:41]3[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=3)[CH2:37][CH2:36]2)[CH2:31][CH2:30]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[C:1]([C:4]1[N:5]=[C:6]([C:24]([CH3:26])=[CH2:25])[C:7]([O:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:8][C:9]=1[NH:45][C:44]1[CH:46]=[CH:47][C:41]([N:38]2[CH2:39][CH2:40][CH:35]([N:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[CH2:36][CH2:37]2)=[CH:42][CH:43]=1)(=[O:3])[NH2:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 580157484-(4-(4-Methyl-1-piperazinyl)-1-piperidinyl)benzenamineHCID 117675582tert-butyl (3R)-3-{[5-carbamoyl-6-chloro-3-(2-hydroxypropan-2-yl)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate

生成物 1

HCID 117675492
tert-butyl (3R)-3-{[5-carbamoyl-6-({-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-3-(prop-1-en-2-yl)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate
収率 65.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of tert-butyl (3R)-3-{[5-carbamoyl-6-chloro-3-(2-hydroxypropan-2-yl)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate (300 mg), 4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (680 mg), diisopropylethylamine (400 μL), and N-methylpyrrolidone (1.2 mL) was reacted in a microwave reaction device at 180° C. for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1), and then washed with diisopropyl ether to obtain tert-butyl (3R)-3-{[5-carbamoyl-6-({-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-3-(prop-1-en-2-yl)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate (304 mg) as a yellow solid.

後処理

  1. customwas reacted in a microwave reaction device at 180° C. for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1)
  6. washwashed with diisopropyl ether

出典と根拠

ORDレコード
ord-c2fa998181cb46b987ee422d602faa4c
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085540B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート