HCID 67496133, compound → HCID 67497106, compound

HRID 2365230Notes

Reaction equation

HRID 2365230 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([CH2:10][CH:11]([C:13]2[N:14]([CH3:25])[N:15]=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)O)=[N:7][C:6]=1[CH3:26])=[O:4]>S(=O)(=O)(O)O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[N:16]=[N:15][N:14]([CH3:25])[C:13]=2/[CH:11]=[CH:10]/[C:8]2[S:9][C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:26])[N:7]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 67496133HCID 67496133, compound

Product 1

HCID 67497106HCID 67497106, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 2-{2-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid methyl ester (204 mg, 0.54 mmol) in sulfuric acid (conc., 3.19 mL) was heated at 160° C. under Ar for 2 h. After cooling to room temperature the mixture was poured into ice and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (165 mg, 88%) as an off white solid. MS: m/e=343.0 [M−H]−.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured into ice
  3. extractionextracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-338f70dd6f124a2687efdd29850cb726
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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