Sulfuric Acid → Ethyl 4-aminopyrrolo[2,1-F][1,2,4]triazine-6-carboxylate

HRID 1500805Notes

Reaction equation

HRID 1500805 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8]C(C#N)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>C(O)C.ClCCl>[NH2:1][C:2]1[C:7]2=[CH:8][C:21]([C:20]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 552974584-Aminopyrrolo[2,1-F][1,2,4]triazine-6-carbonitrile

Product 1

HCID 66641336Ethyl 4-aminopyrrolo[2,1-F][1,2,4]triazine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-aminopyrrolo[2,1-f][1,2,4]triazine-6-carbonitrile (3.9 g, 24.5 mmol; preparation described in PCT Int. Pat. Appl. WO 2007/064883) in ethanol (124.8 ml) was stirred with concentrated sulfuric acid (62.4 ml) at 80° C. overnight. After cooling to rt, the reaction mixture was poured onto 800 g of ice and brought to pH 6-7 with concentrated aq. sodium hydroxide solution. Ethyl acetate (500 ml) and dichloromethane (500 ml) were added to the suspension, and the resulting mixture was filtered over kieselguhr. The organic layer was separated from the aqueous layer. The solid was dissolved in hot water (1 L), and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated. The residue was triturated with an isopropanol/diethylether mixture, and the solid was filtered off yielding 2.5 g (49% of th.) of the title compound.

Workup

  1. filtrationthe resulting mixture was filtered over kieselguhr
  2. customThe organic layer was separated from the aqueous layer
  3. dissolutionThe solid was dissolved in hot water (1 L)
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was triturated with an isopropanol/diethylether mixture
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-2ea6ce13239a4a6bbc6a37c7767bf0e9
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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