Hydrochloric Acid → HCID 89783129, compound

HRID 58068Notes

Reaction equation

HRID 58068 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]#N)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2.[OH-:24].[Na+].Cl.[OH2:27]>CCO>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:27])=[O:24])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 897829826-methoxy-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

Product 1

HCID 89783129HCID 89783129, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6-methoxy-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile (0.5 g, 1.571 mmol) in EtOH (20 mL) was added sodium hydroxide (3.93 mL, 7.86 mmol). The reaction mixture was stirred for 50 minutes at reflux and was subsequently diluted with water and acidified with concentrated HCl. The volatiles were evaporated and the residue was purified by preparative HPLC, eluting with 45% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 4 minutes. The product-containing fractions were combined and the volatiles removed by rotary evaporation to give the title compound.

Workup

  1. temperatureat reflux
  2. customThe volatiles were evaporated
  3. customthe residue was purified by preparative HPLC
  4. washeluting with 45% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 4 minutes
  5. customthe volatiles removed by rotary evaporation

Sources & evidence

ORD record
ord-109f9e00cedb4c108dd5168945f570d3
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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