Cyclopropylamine → 8-Chloro-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-di hydrobenzo[b][1,8]naphthyridine

HRID 344852Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20][N:21](C)[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.[CH:26]1(N)C[CH2:27]1>ClC(Cl)Cl>[Cl:25][C:6]1[C:7]([F:24])=[CH:8][C:9]2[C:4]([CH:5]=1)=[N:3][C:2]1[N:21]([CH:22]3[CH2:27][CH2:26]3)[CH:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12](=[O:13])[C:11]=1[CH:10]=2

Participants

Conditions

Temperature: 78 °C

Procedure

A solution of ethyl 2-(2,7-dichloro-6-fluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (20.6 g) and cyclopropylamine (6 g) in trichloromethane (100 cc) is stirred at a temperature in the region of 20° C. for 24 hours. The reaction mixture is concentrated under reduced pressure (2.7 kPa) at 50° C. The residue is taken up with ethanol (180 Zcc) and DBU (10 g) and the solution obtained heated to a temperature in the region of 78° C. for 4 hours. After cooling to a temperature in the region of 20° C., the precipitate obtained is drained and washed with ethanol (2×60 cc). 8-Chloro-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-di hydrobenzo[b][1,8]naphthyridine (13.65 g) is obtained in the form of a pale yellow solid, m.p. 256° C., which is used without further purification for the subsequent steps.

Workup

concentrationThe reaction mixture is concentrated under reduced pressure (2.7 kPa) at 50° C
customthe solution obtained
temperatureAfter cooling to a temperature in the region of 20° C.
customthe precipitate obtained
washwashed with ethanol (2×60 cc)

Sources & evidence

ORD record: ord-d68db091b88b4b15b5259d6ebaebf681
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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