Acetic Acid → 8-(4-Fluorobenzyl)-10-hydroxy-2,4-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494087Notes

Reaction equation

HRID 494087 reaction equation
[C:1]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:12](=[O:13])[C:7]2=[C:6]([OH:22])[C:5]=1[C:23]([O:25]CC)=O)(=O)[CH3:2].[CH3:28][NH:29][NH2:30].C(O)(=O)C>C(O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]3[C:7](=[C:6]([OH:22])[C:5]4[C:23](=[O:25])[N:29]([CH3:28])[N:30]=[C:1]([CH3:2])[C:4]=43)[C:12]2=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 68865212Ethyl 6-acetyl-2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

Product 1

HCID 546859608-(4-Fluorobenzyl)-10-hydroxy-2,4-dimethyl-7,8-dihydropyrazino-[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-acetyl-2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate (75 mg, 0.2 mmol), methylhydrazine (46 mg, 1 mmol), and a drop of acetic acid in ethanol (4 mL) was heated in a sealed tube at 105° C. overnight. The product mixture was concentrated under vacuum. The residue was recrystallized from methanol to provide the titled product.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-63a98ae66b25457184dc16c5d23a8d1e
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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