N-methyl-2-pyrrolidone → 3-{[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide

HRID 1526175노트

반응식

HRID 1526175 반응식
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][CH:29]([N:32]2[CH:36]=[C:35]([NH2:37])[CH:34]=[N:33]2)[CH2:28][CH2:27]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>[Cl-].[Na+].O.O>[CH3:25][N:26]1[CH2:27][CH2:28][CH:29]([N:32]2[CH:36]=[C:35]([NH:37][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]=[N:33]2)[CH2:30][CH2:31]1

참가 물질

7

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 533023461-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amineHCID 1176669023-Chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide

생성물 1

HCID 1176670793-{[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide수율 52.1%

시약·촉매·용매 2

HCID 962Water용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 3-chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (300 mg), 1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine (184 mg), diisopropylethylamine (291 μL), and N-methylpyrrolidone (3 mL) was reacted in a microwave reaction device at 180° C. for 2 hours. To the reaction mixture were added water and saturated brine, followed by extraction with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1). The obtained solid was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2) to obtain 3-{[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide (212 mg) as a yellow solid.

후처리

  1. customwas reacted in a microwave reaction device at 180° C. for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1)
  6. customThe obtained solid was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2)

출처 및 근거

ORD 기록
ord-1c66a7fc4fa7463c9a78e8797b57f5c9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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