Water → HCID 67732731, compound

HRID 743645Notes

Reaction equation

CS(O)(=O)=O.CS(O)(=O)=O.[NH2:11][C@@H:12]1[CH2:15][NH:14][C@H:13]1[CH3:16].C(N(CC)CC)C.[F:24][C:25]1[C:43](F)=[CH:42][C:28]2=[N:29][C:30]3[N:31]([CH3:41])[CH:32]=[C:33]([C:38]([OH:40])=[O:39])[C:34](=[O:37])[C:35]=3[CH:36]=[C:27]2[CH:26]=1.O>CS(C)=O>[NH2:11][C@@H:12]1[CH2:15][N:14]([C:43]2[C:25]([F:24])=[CH:26][C:27]3[C:28]([CH:42]=2)=[N:29][C:30]2[N:31]([CH3:41])[CH:32]=[C:33]([C:38]([OH:40])=[O:39])[C:34](=[O:37])[C:35]=2[CH:36]=3)[C@H:13]1[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 18 g of trans-3-amino-2-methylazetidine dimethanesulphonate and 12.7 g of triethylamine in 150 cm3 of dimethyl sulphoxide is heated with stirring to approximately 70° C. for 20 minutes. At the same temperature, 14.5 g of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are added in small portions in the course of 10 minutes, and the mixture is heated to approximately 90° C. for 2 hours. After cooling to approximately 20° C., the reaction mixture is poured into 400 cm3 of water at the same temperature. The insoluble matter is drained, washed with twice 100 cm3 of water and twice 100 cm3 of ethanol and recrystallized in 300 cm3 of dimethylformamide. 13.9 g of 8-(trans-3-amino-2-methyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 265°-267° C.

Workup

temperaturethe mixture is heated to approximately 90° C. for 2 hours
temperatureAfter cooling to approximately 20° C.
washwashed with twice 100 cm3 of water and twice 100 cm3 of ethanol
customrecrystallized in 300 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-c22eded1065f4834a4ee220b839cbc68
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556861

Reaction notes

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