Triethylamine → N2-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N1-(cyanomethyl)leucinamide

HRID 1744116Notes

Reaction equation

HRID 1744116 reaction equation
[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][N:5]([CH3:7])[CH:6]=1.C1CN([P+](O[N:34]2N=[N:41][C:36]3C=CC=C[C:35]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([NH:41][CH2:36][C:35]#[N:34])=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69151592N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucine

Product 1

HCID 86594568N2-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N1-(cyanomethyl)leucinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucine (366 mg, 1.26 mmol), PyBOP (725 mg, 1.39 mmol), aminoacetonitrile hydrochloride (257 mg, 2.78 mmol) in dry DMF (15 mL) under dry nitrogen was added triethylamine (0.62 mL, 4.45 mmol) dropwise and the reaction stirred for 2½ hours. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 6/4) to afford N2-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N1-(cyanomethyl)leucinamide.

Workup

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 6/4)

Sources & evidence

ORD record
ord-ca4d055fd75b417dac0ba279b0c59371
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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