Triethylamine → HCID 11703167, compound

HRID 750789Notes

Reaction equation

HRID 750789 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][C@H:9]1[C:16]([OH:18])=O.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:30]2C=CC=C[C:29]=2[N:28]=N1.Cl.NCC#N.C(N(CC)CC)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[CH2:13][CH2:12][C:11]([F:14])([F:15])[CH2:10][C@H:9]1[C:16]([NH:28][CH2:29][C:30]#[N:26])=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 11537016HCID 11537016, compound

Product 1

HCID 11703167HCID 11703167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (1R,2R)-2-(2-bromophenyl)-5,5-difluorocyclohexanecarboxylic acid (820 mg, 2.58 mmol), benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (1.49 g, 2.86 mmol) and aminoacetonitrile hydrochloride (530 mg, 5.73 mmol) in N, N-dimethylformamide (5.0 mL) was cooled to 0° C. and treated with triethylamine (1.26 mL, 9.04 mmol). The resulting slurry was stirred at room temperature for 2.5 hours and then poured into water and extracted with ethyl acetate (3×). The combined extracts were washed with brine and dried (Na2SO4). Concentration in vacuo and chromatography of the residue on silica eluting with 2/3 EtOAc/hexanes yielded (1R,2R)-2-(2-bromophenyl)-N-(cyanomethyl)-5,5-difluorocyclohexanecarboxamide as a faint-yellow foam.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration in vacuo and chromatography of the residue on silica eluting with 2/3 EtOAc/hexanes

Sources & evidence

ORD record
ord-03f87637b6a9481ab47a7a96e8d9e13d
Source dataset
uspto-grants-2008_07
Patent number
US07405229B2

Reaction notes

Loading…