Lithium Hydroxide → HCID 25116529, compound

HRID 1099433Notes

Reaction equation

HRID 1099433 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10]C)=[O:9])=[N:6][CH:7]=1.[F:12][C:13]([F:18])([F:17])[CH2:14][CH2:15][OH:16].C[C:20](C)([O-:22])C.[K+].[OH-].[Li+]>O>[F:12][C:13]([F:18])([F:17])[CH2:14][CH2:15][O:16][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:20][O:22][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 1375123,3,3-Trifluoro-1-propanolHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 2

HCID 25116529HCID 25116529, compoundYield 53%HCID 457898115-Methoxy-2-pyrazinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 53% yield starting from methyl 5-chloropyrazine-2-carboxylate and 3,3,3-trifluoropropan-1-ol. 1 additional equivalent of 3,3,3-trifluoropropan-1-o deprotonated with potassium tert-butoxide was added at 0° C. after stirring 1 h at ambient temperature. Water must have been present because hydrolysis of the ester was performed without adding lithium hydroxide and water. The product was collected by extraction of the acidic water layer with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the title compound in a 74:26 mixture with 5-methoxypyrazine-2-carboxylic acid which was also formed in the reaction; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1 H), 8.30-8.47 (m, 1 H), 4.62 (t, 2 H), 2.78-2.95 (m, 2 H); MS (ESI) m/z 237[M+H+], m/z 235[M−H];

Workup

  1. additionwas added at 0° C.
  2. customThe product was collected by extraction of the acidic water layer with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e99b77f28931458f8cabe6ade26a7189
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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