Neopentylamine → HCID 57917639, compound

HRID 1878359Notes

Reaction equation

HRID 1878359 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[CH3:30].C1C([N+]([O-])=O)=CC=C([Cl-][C:41]([O-])=[O:42])C=1.[CH3:44][C:45]([CH3:49])([CH3:48])[CH2:46][NH2:47]>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:47][CH2:46][C:45]([CH3:49])([CH3:48])[CH3:44])=[O:42])=[C:3]([CH3:30])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 57917707HCID 57917707, compound

Product 1

HCID 57917639HCID 57917639, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-((4-(4-amino-3-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.153 mmols 62.5 mg) in dichloromethane (2 mL) was added 4-nitrophenylchloroformate (0,153 mmol, 30.8 mg). After 1 hour stirring, 2,2-dimethylpropan-1-amine (0.306 mmol, 26.7 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 (11.5 mg).

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-3f0019ab1f13434db0a11b59ce6ca358
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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