Ethyl trifluoroacetate → HCID 49780367, compound

HRID 929510Notes

Reaction equation

HRID 929510 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.[F:22][C:23]([F:30])([F:29])[C:24](OCC)=[O:25]>C1COCC1>[F:22][C:23]([F:30])([F:29])[C:24]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1)=[O:25]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 49780164HCID 49780164, compound

Product 1

HCID 49780367HCID 49780367, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 42 (100 mg, 0.33 mmol) was dissolved in dry THF (1 mL), ethyl trifluoroacetate (30 μl 0.39 mmol) was added and the reaction was refluxed for 18 hours. The reaction was cooled to RT, evaporated and the residue chromatographed from EtOAc to give compound 53 (49 mg, 37%) as a white solid: Mp 150-154° C. 1H NMR (500 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.47 (d, J=9.0 Hz, 2H), 7.22 (d, J=8.6 Hz, 2H), 6.27 (d, J=7.6 Hz, 1H), 4.15 (d, J=13.1 Hz, 1H), 3.80 (d, J=11.1 Hz, 2H), 3.38 (t, J=11.9 Hz, 1H), 3.11 (t, J=12.1 Hz, 1H), 1.94 (t, J=15.2 Hz, 2H), 1.46-1.34 (m, 2H). Purity 100%. HRMS calculated for C15H15F6N3O3+H+ 400.1096. found (ESI(+), [M+H]) 400.1078.

Workup

  1. temperaturethe reaction was refluxed for 18 hours
  2. customevaporated
  3. customthe residue chromatographed from EtOAc

Sources & evidence

ORD record
ord-705d03fa931940559e4e488cc04d5929
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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