Dimethylformamide → HCID 58134647, compound

HRID 444757Notes

Reaction equation

HRID 444757 reaction equation
[F:1][C:2]1[C:3]([F:26])=[C:4]2[O:9][CH2:8][C:7]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[N:6]3[CH:14]=[C:15]([C:23]([OH:25])=[O:24])[C:16](=[O:22])[C:17]([C:18]=1[N+:19]([O-])=O)=[C:5]23.CN(C=O)C>C(O)C.C(O)(=O)C.[Pd]>[NH2:19][C:18]1[C:17]2[C:16](=[O:22])[C:15]([C:23]([OH:25])=[O:24])=[CH:14][N:6]3[C:7]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][O:9][C:4]([C:5]=23)=[C:3]([F:26])[C:2]=1[F:1]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 581347099',10'-difluoro-8'-nitro-7'-oxospiro[cyclopentane-1,3' (2'H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6'-carboxylic acid

Product 1

HCID 58134647HCID 58134647, compoundYield 84,748.203%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of 9′,10′-difluoro-8′-nitro-7′-oxospiro[cyclopentane-1,3′ (2′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylic acid (3.9 g, 0.01 mmol) in ethanol/acetic acid (1:1, v/v, 100 mL) was hydrogenated under atmospheric pressure over 10% Pd/C (390 mg) at 80° C. for 18 h. Then 200 mL of DMF were added and the reaction mixture was heated until it became clear. The catalyst was removed by filtration over Celite, which was washed two times with hot DMF and the combined filtrates were concentrated in vacuo to dryness to yield the title compound (2.85 g, 73%) which was used crude in the next step.

Workup

  1. temperaturethe reaction mixture was heated until it
  2. customThe catalyst was removed by filtration over Celite, which
  3. washwas washed two times with hot DMF
  4. concentrationthe combined filtrates were concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-23b8173d68e145c89c8183301e18d3a7
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

Loading…