Water → HCID 178437586, compound

HRID 1500652Notes

Reaction equation

HRID 1500652 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[N:10]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH3:24])[CH:19]=[CH:18]4)[C:11]([SH:14])=[N:12][N:13]=2)[C:6]([O:25]C)=[CH:5][C:4]=1[O:27]C)[CH3:2].Cl.N1C=CC=CC=1.O>C(OCC)(=O)C>[CH2:1]([C:3]1[C:4]([OH:27])=[CH:5][C:6]([OH:25])=[C:7]([C:9]2[N:10]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH3:24])[CH:19]=[CH:18]4)[C:11]([SH:14])=[N:12][N:13]=2)[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10176127Pyridinium chlorideHCID 178437587HCID 178437587, compound

Product 1

HCID 178437586HCID 178437586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
220 °C

Procedure

A flask was charged with 5-(6-Ethyl-3,5-dimethoxy-pyridin-2-yl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazole-3-thiol (30 mg; 0.08 mmol), and pyridine hydrochloride (2 g). The reaction was put under a nitrogen atmosphere, and heated to 220° C. for forty five minutes, and then cooled. To the flask was then added water (10 mL) and ethyl acetate (10 mL), and the contents were stirred until all solids were dissolved. The organic layer was isolated, washed with water, and all solvent was evaporated under vacuum with heating to give 2-ethyl-6-[5-mercapto-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-pyridine-3,5-diol.

Workup

  1. temperaturecooled
  2. dissolutionwere dissolved
  3. customThe organic layer was isolated
  4. washwashed with water
  5. customall solvent was evaporated under vacuum
  6. temperaturewith heating

Sources & evidence

ORD record
ord-152f429f3d2f4f37af377536f60a0770
Source dataset
uspto-grants-2015_12
Patent number
US09206162B2

Reaction notes

Loading…