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Neopentylamine → 3-((4-(3-Fluoro-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

HRID 1878422
Notes
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Reaction equation

HRID 1878422 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=3)[C:18]([NH:20][C:21]([CH3:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:33].C1C([N+]([O-])=O)=CC=C([Cl-][C:44]([O-])=[O:45])C=1.[CH2:47]([NH2:52])[C:48]([CH3:51])([CH3:50])[CH3:49]>ClCCl>[F:33][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:2]=1[NH:1][C:44]([NH:52][CH2:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:45])[C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=2)[C:18]([NH:20][C:21]([CH3:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[O:19])[CH2:12][CH2:13]1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 579176513-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-y)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

Product 1

HCID 251913773-((4-(3-Fluoro-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-y)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide (0.480 mmol, 224 mg) and 4-nitrophenylchloroformate (0.528 mmol, 108 mg) were stirred together in dichloromethane (2 mL) for 16 hours. Neopentylamine (2.4 mol, 300 μL) was added and the volatiles were removed under vacuum. The residue was purified by silica chromatography to yield the title compound (184 mg). MS (ESI) m/z 580.1 [M+H]+

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-2a64ce9bbebc4949a2ade05d2f704a9f
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes