Hydrochloric Acid → HCID 69947690, compound

HRID 413057Notes

Reaction equation

[OH-].[K+].[F:3][C:4]1[C:24]([N:25]2[CH2:29][CH2:28][CH2:27][C@H:26]2[CH2:30][NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:23][C:7]2[C:8]3[C:9](=[O:22])[C:10]([C:17]([O:19]CC)=[O:18])=[CH:11][N:12]([CH3:16])[C:13]=3[CH:14]=[N:15][C:6]=2[CH:5]=1.Cl>C(O)C.O>[F:3][C:4]1[C:24]([N:25]2[CH2:29][CH2:28][CH2:27][C@H:26]2[CH2:30][NH:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:23][C:7]2[C:8]3[C:9](=[O:22])[C:10]([C:17]([OH:19])=[O:18])=[CH:11][N:12]([CH3:16])[C:13]=3[CH:14]=[N:15][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3.4 cm3 of 1 N aqueous potassium hydroxide was added, with stirring, to a suspension of 0.66 g of ethyl (S)-8-fluoro-4-methyl-1-oxo-9-(2-phenylaminomethylpyrrolidin-1-yl)-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in 15 cm3 of ethanol and 10 cm3 of water. The mixture was heated at about 100° C. for 24 hours. The suspension obtained was acidified by addition of 3.4 cm3 of 1 N aqueous hydrochloric acid. After cooling, the solid was dewatered and washed three times with 50 cm3 of water and dried at about 100° C. for 4 hours at a pressure of 1 kPa. 1 g of (S)-8-fluoro-4-methyl-1-oxo-9-(2-phenylaminomethylpyrrolidin-1-yl)-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid was obtained in the form of an orange-colored solid, which melted at around 250° C.

Workup

customThe suspension obtained
temperatureAfter cooling
washwashed three times with 50 cm3 of water
customdried at about 100° C. for 4 hours at a pressure of 1 kPa

Sources & evidence

ORD record: ord-69d749c0f592402ba5dbd7d748c82530
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

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