HCID 58134630, compound → HCID 58134838, compound

HRID 1396089Notes

Reaction equation

HRID 1396089 reaction equation
[F:1][C:2]1[C:3]([F:27])=[C:4]2[O:9][C:8]3([CH2:12][CH2:11][CH2:10]3)[CH2:7][N:6]3[CH:13]=[C:14]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:15](=[O:21])[C:16]([C:17]=1[N+:18]([O-])=O)=[C:5]23>CN(C=O)C.[Pd]>[NH2:18][C:17]1[C:16]2[C:15](=[O:21])[C:14]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:13][N:6]3[CH2:7][C:8]4([CH2:12][CH2:11][CH2:10]4)[O:9][C:4]([C:5]=23)=[C:3]([F:27])[C:2]=1[F:1]

Participants

4

Reactant 1

HCID 58134630HCID 58134630, compound

Product 1

HCID 58134838HCID 58134838, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 9′,10′-difluoro-8′-nitro-7′-oxo-spiro[cyclobutane-1,2′(3′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (450 mg, 1.15 mmol) and 10% Pd/C (40.5 mg) in DMF (20 mL) was stirred under hydrogen atmosphere (0.3 MPa) at 50° C. for 3 hours. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The resulting solid was dissolved in EtOH—CH2Cl2 (1:5) and filtered. CH2Cl2 was removed, and the resulting precipitate was removed by filtration, washed with EtOH and dried to yield the title compound (270 mg, 67%) as a pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 1.27 (3H, t, J=7.3 Hz), 1.74-1.96 (2H, m), 2.02-2.13 (2H, m), 2.14-2.25 (2H, m), 4.20 (2H, q, J=7.3 Hz), 4.33 (2H, s), 7.33 (2H, brs), 8.43 (1H, s). ESIMS (+): 350[M+H]+.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe resulting solid was dissolved in EtOH—CH2Cl2 (1:5)
  4. filtrationfiltered
  5. customCH2Cl2 was removed
  6. customthe resulting precipitate was removed by filtration
  7. washwashed with EtOH
  8. customdried

Sources & evidence

ORD record
ord-35f24c4f15f140afaded535cc2ebe8f7
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

Loading…