Neopentylamine → HCID 71253456, compound

HRID 1029023Notes

Reaction equation

HRID 1029023 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:36]([NH2:41])[C:37]([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:41][CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:6]

Participants

5

Reactant 3

HCID 79882NeopentylamineHCID 27355882-Bromo-3-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71253456HCID 71253456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-3-methylbenzoic acid (2.150 g, 10 mmol) and HATU (3.80 g, 10.00 mmol) in DMF (20 mL) was stirred for 10 min at RT. Neopentylamine (1.170 mL, 10.00 mmol) was slowly added and the reaction mixture was allowed to stir at RT overnight. The reaction was quenched with 1N HCl and the solution was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (6-50% EtOAc/hexanes). 2-Bromo-3-methyl-N-neopentylbenzamide was isolated as a white solid.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. customthe solution was partitioned between brine and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe remaining residue was purified by flash chromatography (6-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-13b108efd92f4ca0bb6a228bae6f9db3
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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