Dimethylformamide → HCID 11268213, compound

HRID 2109110Notes

Reaction equation

HRID 2109110 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C@H:10]([C:12](O)=O)[CH3:11])=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22])#N.C(Cl)(=O)C(Cl)=O.C[N:32](C=O)C.[NH4+:36].[OH-:37]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:15][CH2:16][C:17]([F:18])([F:20])[F:19])[C@H:10]([C:12]([NH2:32])=[O:37])[CH3:11])=[CH:5][C:4]=1[C:21]([F:22])([F:23])[F:24])#[N:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 86614372HCID 86614372, compound

Product 1

HCID 11268213HCID 11268213, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(3,3,3-trifluoropropyl)alanine (0.020 g, 0.56 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.009 g, 0.07 mmol) and a catalytic amount of DMF. The mixture was heated at 45° C. for 45 min, cooled to rt and added to NH4OH (30% solution, 3 mL). The mixture was stirred for 30 min and then partitioned between EtOAc and 0.1N HCl. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (1-8% MeOH—CH2Cl2 gradient) and the product was crystallized from CH2Cl2-hexanes to give 0.014 g (70% yield) of the title compound as a white solid: MS (ES) m/z 354 (M+1).

Workup

  1. temperaturecooled to rt
  2. custompartitioned between EtOAc and 0.1N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (1-8% MeOH—CH2Cl2 gradient)
  7. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-ca4d87c57248430c8055c3108d900da1
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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