HCID 58134715, compound → HCID 58134649, compound

HRID 444791Notes

Reaction equation

[F:1][C:2]1[C:3]([F:28])=[C:4]2[O:9][CH2:8][C:7]3([CH2:13][CH2:12][O:11][CH2:10]3)[N:6]3[CH:14]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16](=[O:22])[C:17]([C:18]=1[N+:19]([O-])=O)=[C:5]23>CC(O)=O.[Fe]>[NH2:19][C:18]1[C:17]2[C:16](=[O:22])[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14][N:6]3[C:7]4([CH2:13][CH2:12][O:11][CH2:10]4)[CH2:8][O:9][C:4]([C:5]=23)=[C:3]([F:28])[C:2]=1[F:1]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 9′,10′-difluoro-8′-nitro-7′-oxospiro[oxolane-3,3′(2′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (3.15 g, 7.95 mmol) and iron (2.66 mg, 47.7 mmol) in AcOH (40 mL) was stirred at 90° C. for 5 h. After the reaction mixture was concentrated in vacuo, DMF was added and the mixture was filtrated through Celite. The filtrate was poured into water and the resulting precipitate was collected by filtration and dried to yield ethyl 8′-amino-9′,10′-difluoro-7′-oxospiro[oxolane-3,3′(2′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (1.54 g, 53%) as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) 1.25 (3H, t, J=7.3 Hz), 2.29-2.38 (2H, m), 3.72 (1H, d, J=11.0 Hz), 3.90-3.96 (1H, m), 4.06-4.11 (1H, m), 4.15 (1H, d, J=11.0 Hz), 4.19 (2H, q, J=7.3 Hz), 4.32 (1H, d, J=11.0 Hz), 4.41 (1H, d, J=11.0 Hz), 7.42 (2H, brs), 8.34 (1H, s).

Workup

concentrationAfter the reaction mixture was concentrated in vacuo, DMF
additionwas added
filtrationthe mixture was filtrated through Celite
additionThe filtrate was poured into water
filtrationthe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-cfc30e18ae404626be3666bed4c06298
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476261B2

Reaction notes

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