1,8-Diazabicyclo(5.4.0)undec-7-ene → 10-(4-nitro-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid

HRID 1494777Notes

Reaction equation

HRID 1494777 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.Br.[N+:22]([C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][NH:28][CH2:29]2)([O-:24])=[O:23].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N+:22]([C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][N:28]([C:3]1[C:2]([F:1])=[CH:15][C:14]3[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11][N:6]4[CH:7]([CH3:10])[CH2:8][O:9][C:4]=1[C:5]=34)[CH2:29]2)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5342788,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acidHCID 198284974-Nitroisoindoline hydrobromide

Product 1

HCID 1982850710-(4-nitro-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acidYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

185 mg of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid, 176 mg of 4-nitroisoindoline hydrobromide, 164 mg of DBU, and 1.5 ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 131 mg of the target compound.

Sources & evidence

ORD record
ord-1642dc21a4fa460b9bf082ed4507783c
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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