Methylamine → 2-[(4-fluorophenyl)methyl]-8-hydroxy-N-methyl-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxamide

HRID 2114821Notes

Reaction equation

HRID 2114821 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]3[CH:15]=[C:16]([C:19]([O:21]CC)=O)[C:17]([OH:18])=[C:11]3[C:10]2=[O:24])=[CH:6][CH:5]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)(Cl)Cl>[F:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]3[CH:15]=[C:16]([C:19]([NH:2][CH3:1])=[O:21])[C:17]([OH:18])=[C:11]3[C:10]2=[O:24])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 3011068Ethyl 2-[(4-fluorophenyl)methyl]-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 30110702-[(4-fluorophenyl)methyl]-8-hydroxy-N-methyl-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Anhydrous methylamine gas was bubbled through a mixture of ethyl 2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (3.0 g, 9.0 mmol) and anhydrous aluminum chloride (3.0 g, 22.5 mmol) in anhydrous chloroform (45 mL) at 0° C. for 5 minutes. The resultant mixture was heated in a seal tube at 70° C. overnight and concentrated under vacuum. The residue partitioned between aqueous HCl and chloroform. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue partitioned between aqueous HCl and chloroform
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e905ddce903c4a968a0238109eccea5c
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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