Trifluoroacetic acid → HCID 178428036, compound

HRID 906240Notes

Reaction equation

HRID 906240 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:23])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])=[C:12]([CH3:22])[CH:11]=1)=[O:8].C(O)(C(F)(F)F)=O>CC(O)=O>[OH:23][C:6]1[C:7](=[O:8])[N:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]([OH:21])([CH3:19])[CH3:20])=[C:12]([CH3:22])[CH:11]=2)[CH:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57540557N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide

Product 1

HCID 178428036HCID 178428036, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide (11.4 g, 32.2 mmol) and TFA (2.97 mL, 38.6 mmol) in AcOH (120 mL) was stirred at 135° C. in a seal tube for 60 min. After cooling and concentration under vacuum, addition of CH2Cl2 (300 ml) produced a precipitate which was collected by filtration and was washed with CH2Cl2 (150 ml) to yield 3-hydroxy-1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)pyrazin-2(1H)-one (7.19 g, 23.53 mmol, 73.1% yield) as brown solid. MS (M+1=226). 1H NMR (500 MHz, methanol-d3) δ ppm 7.13-7.26 (2H, m), 6.98 (1H, d, J=8.52 Hz), 6.50 (1H, d, J=5.77 Hz), 6.41 (1H, d, J=6.05 Hz), 3.82 (2H, s), 2.29 (3H, s), 1.35 (6H, s).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentration
  3. additionunder vacuum, addition of CH2Cl2 (300 ml)
  4. customproduced a precipitate which
  5. filtrationwas collected by filtration
  6. washwas washed with CH2Cl2 (150 ml)

Sources & evidence

ORD record
ord-1a64c4c31da84a3686eda4131805377d
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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