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

HRID 1526176
Notes
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Reaction equation

HRID 1526176 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

HCID 117666996
6-(2-Hydroxypropan-2-yl)-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide
Yield 21.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f6596e4b961242db919ad37a78454ea4
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085540B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes