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

HRID 747849Notes

Reaction equation

HRID 747849 reaction equation
FC1C=CC([CH2:6][N:7]2CCN3C=C(C(OCC)=O)C(O)=C3C2=O)=CC=1.[F:25][C:26]1[CH:27]=[C:28]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:29][N:30]1[CH2:35][CH2:34][N:33]2[CH:36]=[C:37]([C:40]([O:42]CC)=O)[C:38]([OH:39])=[C:32]2[C:31]1=[O:45]>>[F:25][C:26]1[CH:27]=[C:28]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:29][N:30]1[CH2:35][CH2:34][N:33]2[CH:36]=[C:37]([C:40]([NH:7][CH3:6])=[O:42])[C:38]([OH:39])=[C:32]2[C:31]1=[O:45]

Participants

3

Reactant 2

HCID 3011068Ethyl 2-[(4-fluorophenyl)methyl]-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylateHCID 3011077Ethyl 2-[(3,4-difluorophenyl)methyl]-8-hydroxy-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxylate

Product 1

HCID 30110822-[(3,4-difluorophenyl)methyl]-8-hydroxy-N-methyl-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-7-carboxamide

Procedure

The title compound was prepared using a procedure similar to that described in Example 5, except that ethyl 2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-α]pyrazine-7-carboxylate was substituted with ethyl 2-(3,4-difluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-α]pyrazine-7-carboxylate (Example 12).

Sources & evidence

ORD record
ord-a30614435c2a4d8a922c546506b7f86a
Source dataset
uspto-grants-2008_07
Patent number
US07399763B2

Reaction notes

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