Triethylamine → HCID 20063282, compound

HRID 981208Notes

Reaction equation

C(N(CC)CC)C.Cl.[F:9][CH2:10][CH2:11][NH2:12].Cl[C:14]1[C:23]([C:24]([C:26](=[CH:32]N(C)C)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25])=[CH:22][C:21]2[C:16](=[CH:17][C:18]([Cl:37])=[C:19]([F:36])[CH:20]=2)[N:15]=1>ClC(Cl)Cl>[Cl:37][C:18]1[C:19]([F:36])=[CH:20][C:21]2[C:16]([CH:17]=1)=[N:15][C:14]1[N:12]([CH2:11][CH2:10][F:9])[CH:32]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:24](=[O:25])[C:23]=1[CH:22]=2

Participants

Conditions

Temperature: 75 °C

Procedure

2.7 cm3 of triethylamine are added to a suspension of 1.9 g of 2-fluoroethylamine hydrochloride in 25 cm3 of trichloromethane. 3.5 g of ethyl 2-(2,7-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate are added to the solution obtained at about 20° C. After stirring at this temperature for 16 hours, the solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The residue is taken up in 20 cm3 of ethanol and 3 cm3 of triethylamine and heated at about 75° C., with stirring, for 2 hours. After cooling to about 20° C. the insoluble matter is drained and washed with twice 10 cm3 of ethanol and twice 10 cm3 of diisopropyl ether. 1.9 g of 8-chloro-3-ethoxycarbonyl-7-fluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a yellow solid melting at 268° C., which is used for the subsequent step without further purification

Workup

customobtained at about 20° C
concentrationthe solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C
stirringwith stirring, for 2 hours
temperatureAfter cooling to about 20° C. the insoluble matter
washwashed with twice 10 cm3 of ethanol and twice 10 cm3 of diisopropyl ether

Sources & evidence

ORD record: ord-9a0e1a8ccea241edae7544d375af65a1
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990515

Reaction notes

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