Trifluoroacetic acid → HCID 178490807, compound

HRID 906229Notes

Reaction equation

HRID 906229 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:19])[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:8].C(O)(C(F)(F)F)=O>CC(O)=O>[OH:19][C:6]1[C:7](=[O:8])[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44902124HCID 44902124, compound

Product 1

HCID 178490807HCID 178490807, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N1-(2,2-dimethoxyethyl)-N2-(4-methoxybenzyl)oxalamide (7.5 g, 25.3 mmol) and TFA (2.340 mL, 30.4 mmol) in AcOH (160 mL) was stirred at 135° C. in a seal tube for 1.5 hours. After cooling to RT and removal of the volatiles under vacuum, ethyl ether (150 ml) and sat. aq. NaHCO3 solution (150 ml) were added. The resulting precipitate was collected by filtration, washed with H2O (50 ml) and ether (50 ml) prior to drying under high vacuum to yield 3-hydroxy-1-(4-methoxybenzyl)pyrazin-2(1H)-one (5.30 g, 21.68 mmol, 86% yield) as brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.17 (1H, br. s.), 7.18 (2H, d), 6.81 (2H, d), 6.46 (1H, d, J=5.77 Hz), 6.23 (1H, br. s.), 4.74 (2H, s), 3.24 (1H, s).

Workup

  1. customremoval of the volatiles under vacuum, ethyl ether (150 ml) and sat. aq. NaHCO3 solution (150 ml)
  2. additionwere added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O (50 ml) and ether (50 ml)
  5. customto drying under high vacuum

Sources & evidence

ORD record
ord-defea5946cf1487fbd453424fa67670d
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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