Neopentylamine → HCID 57917621, compound

HRID 1878362Notes

Reaction equation

HRID 1878362 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]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.C1C([N+]([O-])=O)=CC=C([Cl-][C:44]([O-])=[O:45])C=1.[CH3:47][C:48]([CH3:52])([CH3:51])[CH2:49][NH2:50]>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:44]([NH:50][CH2:49][C:48]([CH3:52])([CH3:51])[CH3:47])=[O:45])=[CH:3][C:4]=3[C:30]([F:32])([F:33])[F:31])[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 57917608HCID 57917608, compound

Product 1

HCID 57917621HCID 57917621, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-((4-(4-amino-2-(trifluoromethyl)benzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.123 mmol, 57 mg) in dichloromethane (2 mL) was added 4-nitrophenylchloroformate (0.123 mmol, 24.84 mg). After 1 hour stirring, 2,2-dimethylpropan-1-amine (0.123 mmol, 10.74 mg) was added and stirring was continued for 1 hour. The reaction was concentrated under reduced pressure and the residue dissolved in methanol (1 mL). Purification by basic reverse phase HPLC gave the title compound (27 mg).

Workup

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

Sources & evidence

ORD record
ord-7260f448dfa44d7a8d2bbbb006574150
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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