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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1267609Generated: October 26, 2026

Acetonitrile → 7-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

https://huagongshe.com/reaction/1267609

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetonitrileHCID 6342—
ReactantTriethylamineHCID 8471—
Reactant5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 13910947—
Reactant2,6-Diazaspiro[3.4]octane-2-carboxylic acid, 8-(methoxyimino)-, 1,1-dimethylethyl esterHCID 54547656—
SolventDimethylformamideHCID 6228—
Product7-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acidHCID 5434966330.9%

Reaction Steps

1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid, 1.05 g of t-butyl 8-(methoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 4 g of AmberliteR IRA-420 were added to 20 ml of acetonitrile and thereto 2 ml of triethylamine was added by dropping. The mixture was refluxed for 5 days and then 2 ml of dimethylformamide was added thereto. The resulting mixture was stirred for 1 hour and thus precipitated solid was filtered off. The filtrate was concentrated under the reduced pressure and then to the resulting residue 10 ml of acetonitrile was added and stirred for 1 hour. The precipitated solid was filtered and dried to give 420 mg of the titled compound (yield: 30.9%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06552196B2
Source datasetuspto-grants-2003_04
ORD IDord-c4ee7c21158c4b79a29da56c7ddda376
Source noteuspto-grants-2003_04