1,8-Diazabicyclo(5.4.0)undec-7-ene → 10-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

HRID 1589568Notes

Reaction equation

HRID 1589568 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.Cl.Cl.[CH:23]12[CH2:30][CH2:29][CH:26]([NH:27][CH2:28]1)[CH2:25][NH:24]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:23]12[CH2:30][CH2:29][CH:26]([NH:27][CH2:28]1)[CH2:25][N:24]2[C:3]1[C:2]([F:1])=[CH:15][C:14]2[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11][N:6]3[CH:7]([CH3:10])[CH2:8][O:9][C:4]=1[C:5]=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 229243902,5-Diazabicyclo(2.2.2)octane dihydrochloride

Product 1

HCID 1356584010-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acidYield 26.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.56 g (2.0 mmol) of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 0.41 g (2.2 mmol) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride, 0.90 ml (6.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 25 ml of acetonitrile was heated under reflux for 18 hours. The solution was evaporated to dryness and the residue was triturated with methanol and filtered to give 0.20 g of the title compound, 260°-265° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe solution was evaporated to dryness
  3. customthe residue was triturated with methanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-004445253279438d81facaf8f68fee8b
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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