Neopentylamine → HCID 57917620, compound

HRID 1878340Notes

Reaction equation

HRID 1878340 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])=[C:4]([CH3:30])[CH:3]=1.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])=[CH:3][C:4]=3[CH3:30])[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 57917581HCID 57917581, compound

Product 1

HCID 57917620HCID 57917620, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-2-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (100 mg, 0.24 mmol) and 4-nitrophenylchloroformate (49 mg, 0.24 mmol) were stirred in dichloromethane (2 mL) for 30 minutes. Neopentylamine (64 mg, 0.73 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 (31 mg). MS (ESI) m/z 522.7 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-d4f971524a6540ae92281766efb6bbb9
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…