Water → 2-Pyrazinecarboxylic acid, 5-(fluoromethoxy)-, methyl ester

HRID 1693168Notes

Reaction equation

HRID 1693168 reaction equation
[F:1][C:2]1C=CC=CC=1[C@]12COC[C@H]1CSC(NC(=O)C1C=CC=CC=1)=N2.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:32][C:33]1[N:34]=[CH:35][C:36]([C:39]([O:41][CH3:42])=[O:40])=[N:37][CH:38]=1.O>CN(C)C=O>[F:1][CH2:2][O:32][C:33]1[N:34]=[CH:35][C:36]([C:39]([O:41][CH3:42])=[O:40])=[N:37][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57827147(+/-)-N-[(4aS*,7aS*)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]benzamideHCID 178498852HCID 178498852, compound

Product 1

HCID 574756772-Pyrazinecarboxylic acid, 5-(fluoromethoxy)-, methyl esterYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Fluoromethyl toluene-4-sulfonate (Journal of Labelled Compounds & Radiopharmaceuticals, 46 (6), 555-566; 2003) (344 mg) and cesium carbonate (824 mg) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (130 mg) in N,N-dimethylformamide (2.0 mL). The reaction solution was stirred at 70° C. for five hours and 30 minutes and then cooled to room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (18.0 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-df5837f67098440bbc9c0b6a4c7c9c21
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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