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

HRID 1526165노트

반응식

HRID 1526165 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-783e8825540443a9865f773491f9c967
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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