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1-(3-Aminopropyl)-4-methylpiperazine → 6-[6-[3-(4-Methyl-piperazin-1yl)-propylamino]-pyrimidin-4-yloxy]-naphtalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-Phenyl)-2H-pyrazol-3-yl]-amide

HRID 1094523
Notes
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Reaction equation

HRID 1094523 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]1>CCO>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][C:31]4[CH:36]=[C:35]([NH:38][CH2:39][CH2:40][CH2:41][N:42]5[CH2:43][CH2:44][N:45]([CH3:48])[CH2:46][CH2:47]5)[N:34]=[CH:33][N:32]=4)=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 866386206-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-amide

Product 1

HCID 236529296-[6-[3-(4-Methyl-piperazin-1yl)-propylamino]-pyrimidin-4-yloxy]-naphtalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-Phenyl)-2H-pyrazol-3-yl]-amide

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

100 mg (0.19 mMol) 6-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-amide (Step 20.1) and 73 μl (0.42 mMol) 1-(3-aminopropyl)-4-methylpiperazine are dissolved in 5 ml EtOH. The reaction mixture is stirred at reflux for 30 h. It is worked up by removal of all volatiles under reduced pressure. The remaining crude product is purified by flash chromatography (combi-flash: 14 g column, CH2Cl2/MeOH; gradient 0-20% MeOH) to give the title compound as a yellow solid: m.p.: 131-133° C.

Workup

  1. temperatureat reflux for 30 h
  2. customIt is worked up by removal of all volatiles under reduced pressure
  3. customThe remaining crude product is purified by flash chromatography (combi-flash: 14 g column, CH2Cl2/MeOH; gradient 0-20% MeOH)

Sources & evidence

ORD record
ord-6833600e9aef4a67bef0b16a2cda6ad4
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes