Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 67495517, compound

HRID 2365238Notes

Reaction equation

HRID 2365238 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[CH3:16][N:17]1[C:21]([CH:22]=[O:23])=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:19]=[N:18]1>C1COCC1>[OH:23][CH:22]([C:21]1[N:17]([CH3:16])[N:18]=[N:19][C:20]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 86664842HCID 86664842, compoundHCID 178418339Butyllithium

Product 1

HCID 67495517HCID 67495517, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

To a suspension of 2,4-dimethylthiazole-5-carboxylic acid (157 mg, 1.0 mmol) in THF (8 mL) was added dropwise n-BuLi (1.6 M in hexanes, 1.25 mL, 2.0 mmol) under Ar at −75° C. The brown suspension was stirred at −75° C. for 2 h and then a solution of 3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazole-4-carbaldehyde (188 mg, 1.0 mmol) in THF (3 mL) was added at −75° C. and the brown suspension was stirred at −75° C. for 2 h. The mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL), allowed to warm to room temperature. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by recrystallisation from ethylacetate-heptane afforded the title compound (288 mg, 83%) as a light red solid. MS: m/e=344.0 [M−H]−.

Workup

  1. stirringthe brown suspension was stirred at −75° C. for 2 h
  2. customThe mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL)
  3. temperatureto warm to room temperature
  4. additionThe mixture was then poured into saturated ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification
  11. customby recrystallisation from ethylacetate-heptane

Sources & evidence

ORD record
ord-583922f8c6a04cf5b1f626b46a4fdfd2
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

Loading…