Triethylamine → 2-[(4-bromobenzyl)oxy]-N-(cyanomethyl)-4-methylpentanamide

HRID 1744068Notes

Reaction equation

HRID 1744068 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[NH2:19][CH2:20][C:21]#[N:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH:22][CH2:21][C:20]#[N:19])=[O:11])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 222357912-[(4-Bromobenzyl)oxy]4-methylpentanoic acid

Product 1

HCID 222359802-[(4-bromobenzyl)oxy]-N-(cyanomethyl)-4-methylpentanamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(4-bromobenzyl)oxy]4-methylpentanoic acid in DMF (15 mL) was added aminoacetonitrile hydrochloride (1.9 g, 20.6 mmoles) and HATU (5 g, 13.3 mmoles). After stirring for one minute, triethylamine (5.3 mL, 38.3 mmoles) was added in one portion. The reaction was stirred overnight, diluted with ethyl acetate and water. The organic phase was separated and washed twice with 1.2 N hydrochloric acid, brine and dried over magnesium sulfate. After concentration under reduced pressure, 2-[(4-bromobenzyl)oxy]-N-(cyanomethyl)-4-methylpentanamide was obtained.

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe organic phase was separated
  3. washwashed twice with 1.2 N hydrochloric acid, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-76a11532c5244d5ea10f5116818bb242
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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