Neopentylamine → N-tert-Butyl-3-((4-(3-fluoro-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878331Notes

Reaction equation

HRID 1878331 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:30].C1C([N+]([O-])=O)=CC=C([Cl-][C:41]([O-])=[O:42])C=1.[CH2:44]([NH2:49])[C:45]([CH3:48])([CH3:47])[CH3:46]>ClCCl>[C:21]([NH:20][C:18](=[O:19])[C:17]1[CH:25]=[CH:26][CH:27]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[CH:29][C:2]([NH:1][C:41]([NH:49][CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:42])=[C:3]([F:30])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 668785283-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 25191116N-tert-Butyl-3-((4-(3-fluoro-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)benzamideYield 11.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (175 mg, 0.424 mmol) and 4-nitrophenylchloroformate (85 mg, 0424 mmol) were stirred in dichloromethane (2 mL) for 30 minutes. Neopentylamine (110 mg, 1.272 mmol) was added and the reaction stirred at room temperature for 2 hours. The reaction was concentrated under vacuum. The resulting residue was purified by acidic reverse phase HPLC to afford the title compound (26 mg).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customThe resulting residue was purified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-8bf743ab101d41beb92945aca4558abe
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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