(S)-8-(benzylthio)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid → HCID 14501368, compound

HRID 1904601Notes

Reaction equation

HRID 1904601 reaction equation
C(S[C:9]1[C:22]2[C:21](=[O:23])[C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:14]3[C@@H:15]([CH3:18])[CH2:16][O:17][C:12]([C:13]=23)=[C:11]([C:27]2[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=2)[C:10]=1[F:35])C1C=CC=CC=1>[Ni].C(O)C>[CH3:34][C:29]1[CH:28]=[C:27]([C:11]2[C:10]([F:35])=[CH:9][C:22]3[C:21](=[O:23])[C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:14]4[C@@H:15]([CH3:18])[CH2:16][O:17][C:12]=2[C:13]=34)[CH:32]=[C:31]([CH3:33])[N:30]=1

Participants

4

Reactant 1

HCID 14501371(S)-8-(benzylthio)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid

Product 1

HCID 14501368HCID 14501368, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

It is further contemplated that (S)-8-(benzylthio)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid can be treated with Raney nickel in ethanol to give (S)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid, the compound of Example 3(c).

Sources & evidence

ORD record
ord-d49fcbabbfd8409585e47ee4f835ad0c
Source dataset
uspto-grants-1989_06
Patent number
US04839355

Reaction notes

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