Potassium Carbonate → 6-(2-Hydroxypropan-2-yl)-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide

HRID 1526176노트

반응식

HRID 1526176 반응식
Cl[C:2]1[C:3]([C:22]([NH2:24])=[O:23])=[N:4][C:5]([C:18]([OH:21])([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.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)(C)(C)C>[OH:21][C:18]([C:5]1[N:4]=[C:3]([C:22]([NH2:24])=[O:23])[C:2]([NH:36][C:35]2[CH:34]=[CH:33][C:32]([N:29]3[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]3)=[CH:38][CH:37]=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)([CH3:20])[CH3:19]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 1176669023-Chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide

생성물 1

HCID 1176669966-(2-Hydroxypropan-2-yl)-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide수율 21.1%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6212Chloroform용매HCID 6386tert-Butanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-chloro-6-(2-hydroxypropan-2-yl)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (1 g), 4-(4-methylpiperazin-1-yl)aniline (542 mg), tris(dibenzylideneacetone)dipalladium (0) (130 mg), dicyclohexyl (2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (135 mg), potassium carbonate (1.29 g), and tert-butanol (5 mL) was stirred at 80° C. for 5 days. The reaction mixture was left to be cooled and then diluted with chloroform, and the insoluble matter was separated by filtration. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=100:0:0-300:10:1) to obtain 6-(2-hydroxypropan-2-yl)-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (303 mg) as a yellow solid.

후처리

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. customthe insoluble matter was separated by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=100:0:0-300:10:1)

출처 및 근거

ORD 기록
ord-f6596e4b961242db919ad37a78454ea4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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