Hydrochloric Acid → 5-(Thiazol-4-ylmethoxy)pyrazine-2-carboxylic acid

HRID 1526598Notes

Reaction equation

HRID 1526598 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([O:16]C)=[O:15])=[N:12][CH:13]=2)[N:3]=[CH:2]1.[OH-].[Na+].Cl>O1CCOCC1>[S:1]1[CH:5]=[C:4]([CH2:6][O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[N:12][CH:13]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90389321Methyl 5-(thiazol-4-ylmethoxy)pyrazine-2-carboxylate

Product 1

HCID 903894645-(Thiazol-4-ylmethoxy)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 5-(thiazol-4-ylmethoxy)pyrazine-2-carboxylate (0.7606 g, 3.03 mmol) in 1,4-dioxane (15.14 ml) was added a 1 N solution of sodium hydroxide (4.54 ml, 4.54 mmol) at rt. The reaction mixture was allowed to stir for 16 hours. Hydrogen chloride (4.0M solution in 1,4-dioxane; 1.135 ml, 4.54 mmol, Sigma Aldrich) was added and after 10 minutes, the reaction mixture was concentrated in vacuo to give the title compound. MS m/z=237.9 [M+H]+. Calculated for C9H7N3O3S: 237.021. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.59 (s, 2H) 7.86 (d, J=1.96 Hz, 1H) 8.45 (d, J=1.17 Hz, 1H) 8.83 (d, J=1.37 Hz, 1H) 9.14 (d, J=1.96 Hz, 1H)

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a06f49cd73954062a40eb6f2439804f1
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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