Hydrochloric Acid → 8-(4-(aminomethyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

HRID 1854875Notes

Reaction equation

HRID 1854875 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][N:19]3[C:24]([C:25]=2[CH3:26])=[C:23]([CH:27]2[CH2:29][CH2:28]2)[CH:22]=[C:21]([C:30]([OH:32])=[O:31])[C:20]3=[O:33])=[CH:12][C:11]=1[F:34])=O)(C)(C)C.[ClH:35].O1CCOCC1>C(#N)C>[ClH:35].[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][N:19]3[C:24]([C:25]=2[CH3:26])=[C:23]([CH:27]2[CH2:28][CH2:29]2)[CH:22]=[C:21]([C:30]([OH:32])=[O:31])[C:20]3=[O:33])=[CH:12][C:11]=1[F:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866965858-(4-((tert-butoxycarbonylamino)methyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

Product 1

HCID 866965868-(4-(aminomethyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-(4-((tert-Butoxycarbonylamino)methyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid (24 mg, 0.051 mmol) was dissolved in acetonitrile (4 mL). HCl 4M in dioxane (1 mL, 4 mmol) was added. The mixture was stirred for 4 h and a suspension was formed affording after filtration the title compound EXAMPLE 49 as a yellow solid (17.7 mg, 86%). ESI-MS m/z: 453 (M+H)+.

Workup

  1. customa suspension was formed
  2. customaffording
  3. filtrationafter filtration the title compound EXAMPLE 49 as a yellow solid (17.7 mg, 86%)

Sources & evidence

ORD record
ord-8825d5af176a43dc8ef328fad7b23de7
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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