Diisopropylethylamine → 6-Ethyl-3-{[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide

HRID 1526165ノート

反応式

HRID 1526165 の反応式
Cl[C:2]1[C:3]([C:20]([NH2:22])=[O:21])=[N:4][C:5]([CH2:18][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.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[N:35]=[CH:34][C:33]([NH2:36])=[CH:32][N:31]=2)[CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(OCC)(=O)C>[CH2:18]([C:5]1[N:4]=[C:3]([C:20]([NH2:22])=[O:21])[C:2]([NH:36][C:33]2[CH:32]=[N:31][C:30]([N:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)=[N:35][CH:34]=2)=[N:7][C:6]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH3:19]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 568284122-(4-Methylpiperazin-1-yl)pyrimidin-5-amineHCID 897091113-Chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide

生成物 1

HCID 1176670526-Ethyl-3-{[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide収率 52.5%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (300 mg), 2-(4-methylpiperazin-1-yl)pyrimidine-5-amine (198 mg), and diisopropylethylamine (318 μL) in N-methylpyrrolidone (1.5 mL) was heated at 120° C. for 18 hours. The reaction mixture was cooled, and then diluted with ethyl acetate, and the organic phase was washed with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous anunonia=1:0:0-95:4.5:0.5) to obtain 6-ethyl-3-{[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (234 mg) as a yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washthe organic phase was washed with water and saturated brine
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous anunonia=1:0:0-95:4.5:0.5)

出典と根拠

ORDレコード
ord-783e8825540443a9865f773491f9c967
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…