HCID 67496360, compound → HCID 67496330, compound

HRID 2365233Notes

Reaction equation

HRID 2365233 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([CH2:10][CH:11]([C:13]2[N:14]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:15]=[N:16][C:17]=2[CH3:18])O)=[N:7][C:6]=1[CH3:26])=[O:4]>S(=O)(=O)(O)O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([N:14]2[C:13](/[CH:11]=[CH:10]/[C:8]3[S:9][C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:26])[N:7]=3)=[C:17]([CH3:18])[N:16]=[N:15]2)=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 67496360HCID 67496360, compound

Product 1

HCID 67496330HCID 67496330, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 2-{2-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid methyl ester (355 mg, 0.94 mmol) in sulfuric acid (conc, 5.9 mL) was heated at 160° C. under Ar for 30 min. 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 (249 mg, 77%) as an grey solid. MS: m/e=345.1 [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-da76bc3332ec4b32bcf2f9c1b7e38695
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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