Neopentylamine → HCID 57917709, compound

HRID 1878360Notes

Reaction equation

HRID 1878360 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[O:30][CH3:31].C1C([N+]([O-])=O)=CC=C([Cl-][C:42]([O-])=[O:43])C=1.[CH3:45][C:46]([CH3:50])([CH3:49])[CH2:47][NH2:48]>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:42]([NH:48][CH2:47][C:46]([CH3:50])([CH3:49])[CH3:45])=[O:43])=[C:3]([O:30][CH3:31])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 57917630HCID 57917630, compound

Product 1

HCID 57917709HCID 57917709, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-((4-(4-amino-3-methoxybenzoyl)piperazin-1-y)methyl)-N-tert-butylbenzamide (0.155 mmol, 66 mg) in dichloromethane (2 mL) was added 4-nitrophenylchloroformate (0.155 mmol, 31.3 mg). After 1 hour stirring, 2,2-dimethylpropan-1-amine (0.311 mmol, 27.1 mg) was added and stirring continued for 1 hour. The reaction was concentrated under vacuum and the residue dissolved in methanol (1 mL). Purification by basic reverse phase HPLC gave the title compound (35 mg). MS (ESI) m/z 539.0 [M+H]+

Workup

  1. stirringstirring
  2. waitcontinued for 1 hour
  3. concentrationThe reaction was concentrated under vacuum
  4. dissolutionthe residue dissolved in methanol (1 mL)
  5. customPurification by basic reverse phase HPLC

Sources & evidence

ORD record
ord-ebdc565402d0455b9902623fdbe1b548
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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