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

HRID 1526176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526176
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]

Komponenten

8

Edukt 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

Produkt 1

HCID 1176669966-(2-Hydroxypropan-2-yl)-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamideAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6212ChloroformLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f6596e4b961242db919ad37a78454ea4
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085540B2

Notizen zur Reaktion

Wird geladen…