1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534816Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Br.Br.[C:23]12[CH2:30][NH:29][CH2:28][C:27]=1[CH2:26][NH:25][CH2:24]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:25]4[CH2:26][C:27]5[CH2:28][NH:29][CH2:30][C:23]=5[CH2:24]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

0.4 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.8 g of 3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide and 0.8 ml of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) were suspended in 30 ml of acetonitrile and the suspension was refluxed in 100° C. oil bath for 8 hours. The reaction mixture was kept overnight at room temperature. The produced precipitate was filtered and washed with methanol. 0.35 g of the title compound was obtained (yield 67%)

Workup

filtrationThe produced precipitate was filtered
washwashed with methanol

Sources & evidence

ORD record: ord-5c40eadfc47141a786a7f64aeaae80c9
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091384

Reaction notes

Loading…