Water → 8-(3-Dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 743638Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].Cl.Cl.[CH3:26][N:27]([CH3:32])[CH:28]1[CH2:31][NH:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+].O>CS(C)=O>[CH3:26][N:27]([CH3:32])[CH:28]1[CH2:31][N:30]([C:18]2[C:19]([F:21])=[CH:20][C:10]3[C:11]([CH:17]=2)=[N:12][C:13]2[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7](=[O:23])[C:8]=2[CH:9]=3)[CH2:29]1

Participants

Conditions

Temperature: 95 °C

Procedure

A suspension of 2 g of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine, 1.2 g of 3-(dimethylamino)azetidine dihydrochloride and 1.5 g of sodium carbonate in 30 cm3 of dimethyl sulphoxide is heated with stirring to a temperature in the region of 95° C. for 5 hours. After cooling to approximately 20° C., the reaction mixture is treated with 60 cm3 of water. The insoluble matter is drained and washed with 3 times 20 cm3 of water. 2 g of 8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine are obtained in the form of a yellow solid, melting point 224° C., which is used without further purification for the subsequent steps.

Workup

temperatureis heated
temperatureAfter cooling to approximately 20° C.
washwashed with 3 times 20 cm3 of water

Sources & evidence

ORD record: ord-36de64b5b2d542e599da2546da480dd1
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556861

Reaction notes

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