Hydrochloric Acid → Pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid

HRID 1773531Notes

Reaction equation

HRID 1773531 reaction equation
C([O:3][C:4]([C:6]1[N:14]2[C:9]([CH:10]=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1.N1C=CC=CC=1.O>[N:13]1[N:14]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=[C:9]2[CH:10]=[N:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58056327Ethyl pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate

Product 1

HCID 58056223Pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acidYield 43.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66926435Pyridine waterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid ethyl ester (40 mg) and an aqueous solution of sodium hydroxide (6 M, 1 mL) in a mixture of tetrahydrofuran and methanol (1/1, 1 mL) was heated at 70° C. for 1 hour. The reaction mixture was then cooled, acidified by addition of an aqueous solution of hydrochloric acid (6 M) and evaporated under reduced pressure. The residue was dissolved in a mixture of dichloromethane and water (10/1, 5.5 mL), the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 15 mg of pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of dichloromethane and water (10/1, 5.5 mL)
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dab345ee935c400b9df6830b9783ab46
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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