Carbon Tetrachloride → HCID 57633751, compound

HRID 2109097Notes

Reaction equation

HRID 2109097 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:10][C:11]([NH2:13])=O)=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCCl>[C:11]([CH2:10][N:9]([CH2:14][C:15]([F:16])([F:18])[F:17])[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:19]([F:21])([F:22])[F:20])[CH:5]=1)#[N:13]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 11472813GSK232420A

Product 1

HCID 57633751HCID 57633751, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
87 °C

Procedure

A mixture of N2-[4-cyano-3-(trifluoromethyl)phenyl]-N2-(2,2,2-trifluoroethyl)glycinamide (0.060 g, 0.18 mmol), CCl4 (0.5 mL), DCE (4.5 mL) and polymer-supported triphenyl phosphine (3 mmol/g, 0.123 g, 0.36 mmol) was heated at 87° C. for 3 h. Upon cooling, the resin was filtered off, washed thoroughly with CHCl3 and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient) and the product was crystallized from CH2Cl2-hexanes to give the title compound as a white solid (0.030 g, 55% yield): 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=8.6 Hz, 1H), 7.20 (d, J=2.6 Hz, 1H), 7.09 (dd, J=8.6, 2.6 Hz, 1H), 4.38 (s, 2H), 4.06 (q, J=8.2 Hz, 2H); MS (ES) m/z 308 (M+1).

Workup

  1. temperatureUpon cooling
  2. filtrationthe resin was filtered off
  3. washwashed thoroughly with CHCl3
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient)
  6. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-37fa726c33ca45f0bbc7ed8d31e15289
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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