Hydrochloric Acid → HCID 56961102, compound

HRID 1478311Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([F:35])=[CH:17][N:18]3[C:23]([C:24]=2[CH3:25])=[C:22]([CH:26]2[CH2:28][CH2:27]2)[CH:21]=[C:20]([C:29]([O:31]CC)=[O:30])[C:19]3=[O:34])=[CH:11][C:10]=1[F:36])=O)(C)(C)C.Cl.[OH-].[Na+]>C1COCC1>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([F:35])=[CH:17][N:18]3[C:23]([C:24]=2[CH3:25])=[C:22]([CH:26]2[CH2:28][CH2:27]2)[CH:21]=[C:20]([C:29]([OH:31])=[O:30])[C:19]3=[O:34])=[CH:11][C:10]=1[F:36]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 8-(4-(tert-butoxycarbonylamino)-3-fluoro-phenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (260 mg, 0.52 mmol) in a 4N hydrochloric acid solution (20 mL). The mixture was stirred for 20 min at 50° C. The product was lyophilized and dissolved in a mixture of THF (1 mL) and of an aqueous 4N sodium hydroxide solution (1.31 mL, 5.2 mmol) before being irradiated at 140° C. in a microwave oven for 10 min. The product was purified by preparative HPLC yielding compound 17 8-(4-amino-3-fluoro-phenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-quinolizine-3-carboxylic acid (5.1 mg, 2.5%).

Workup

custombefore being irradiated at 140° C. in a microwave oven for 10 min
customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-6107743f6aa84ff3949dae90544f09eb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403818B2

Reaction notes

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