2,5-Diethoxyoxolanato → HCID 2781696, compound

HRID 1192780Notes

Reaction equation

HRID 1192780 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.C(O[CH:16]1[CH2:20][CH2:19][CH:18](OCC)O1)C>C(O)(=O)C>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:16]=[CH:20][CH:19]=[CH:18]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 955002,5-DiethoxyoxolanatoHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 2781696HCID 2781696, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound was prepared according to Colotta et al. J. Med. Chem. 2006, 49, 6015. A solution of 4-trifluoromethoxyphenyl amine (500 milligrams (mg), 2.82 millimoles (mmol), 1.00 equivalent (eq)) and 2,5-diethoxy tetrahydrofuran (452 mg, 2.82 mmol, 1.00 eq) in glacial acetic acid (20 milliliters (mL)) was heated at 90° C. for 1 hour (h) before being dried onto silica gel. The residue was then slurried in refluxing hexane, filtered hot, and concentrated to dryness affording the desired intermediate (519 mg, 81%).

Workup

  1. customThe compound was prepared
  2. custombefore being dried onto silica gel
  3. temperaturein refluxing hexane
  4. filtrationfiltered hot
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-973cf95be1bd4164b2a14f48b7dc6286
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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