Trifluoroacetic acid → HCID 89524959, compound

HRID 1466020Notes

Reaction equation

HRID 1466020 reaction equation
ClC[C:3]([N:5]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([C:21]#[N:22])[CH:15]=1)[CH2:6][CH2:7][NH:8][C:9](=O)[O-])=[O:4].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][N:5]2[CH2:6][CH2:7][NH:8][CH2:9][C:3]2=[O:4])=[CH:15][C:16]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131732670HCID 131732670, compound

Product 1

HCID 89524959HCID 89524959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{(chloroacetyl) [2-(3-cyano-4-fluorophenyl)ethyl]amino}ethyl)carbamate (0.12 g, 0.31 mmol) and TFA in 5 mL of DCM was stirred at room temperature for 1 h. The solvent was evaporated. The residue was dissolved in 40 mL of ethanol and K2CO3 (0.13 g, 0.93 mmol) was added. The resulting mixture was refluxed under N2 overnight, cooled to room temperature, and filtered. The filtrate was evaporated and the residue was purified with preprep-HPLC to give 2-Fluoro-5-[2-(2-oxopiperazin-1-yl)ethyl]benzonitrile. 1H-NMR (400 MHz, CDCl3) δ: 7.41˜7.44 (m, 2H), 7.07˜7.12 (m, 1H), 3.51˜3.53 (m, 4H), 3.18˜3.22 (m, 2H), 2.99˜3.04 (m, 2H), 2.75˜2.86 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in 40 mL of ethanol
  3. temperatureThe resulting mixture was refluxed under N2 overnight
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was purified with preprep-HPLC

Sources & evidence

ORD record
ord-257a6a8b33a0491eb0138db440bc64fa
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…