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

HRID 1878420Notes

Reaction equation

HRID 1878420 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][CH:3]=1.C1C([N+]([O-])=O)=CC=C([Cl-][C:43]([O-])=[O:44])C=1.[CH2:46]([NH2:51])[C:47]([CH3:50])([CH3:49])[CH3:48]>ClCCl>[CH2:46]([NH:51][C:43](=[O:44])[NH: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:24])([F:25])[F:23])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)[C:47]([CH3:50])([CH3:49])[CH3:48]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 668787853((4-(4-Aminobenzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

Product 1

HCID 251912503-((4-(4-(3-Neopentylureido)benzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3((4-(4-Aminobenzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide (0.129 mmol, 58 mg) and 4-nitrophenylchloroformate (0.142 mmol, 29 mg) were stirred together in dichloromethane (1 mL) for 16 hours. After this time neopentylamine (0.259 mmol, 32 μL) was added. The volatiles were removed under vacuum and this residue was purified by silica chromatography to yield the title compound (50 mg). MS (ESI) m/z 562.5 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-0d9a782474204303a159989708f6f019
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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