Hydrochloric Acid → 8-[4-(Aminomethyl)-3-fluoro-phenyl]-1-cyclopropyl-9-methyl-4-oxoquinolizine-3-carboxylic acid

HRID 1478310Notes

Reaction equation

HRID 1478310 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][N:26]3[C:31]([C:32]=2[CH3:33])=[C:30]([CH:34]2[CH2:36][CH2:35]2)[CH:29]=[C:28]([C:37]([OH:39])=[O:38])[C:27]3=[O:40])=[CH:19][C:18]=1[F:41])=O)(C)(C)C>C(#N)C>[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][N:26]3[C:31]([C:32]=2[CH3:33])=[C:30]([CH:34]2[CH2:35][CH2:36]2)[CH:29]=[C:28]([C:37]([OH:39])=[O:38])[C:27]3=[O:40])=[CH:19][C:18]=1[F:41]

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 569609568-[4-(Aminomethyl)-3-fluoro-phenyl]-1-cyclopropyl-9-methyl-4-oxoquinolizine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4M hydrochloric acid in dioxane (1 mL, 4 mmol) was added to a solution of 8-(4-((tert-butoxycarbonylamino)methyl)-3-fluorophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid (24 mg, 0.051 mmol) in ACN (4 mL). The mixture was stirred for 4 h and a suspension was formed. The product compound 4 was collected by filtration (17.7 mg, 78%).

Workup

  1. customa suspension was formed
  2. filtrationThe product compound 4 was collected by filtration (17.7 mg, 78%)

Sources & evidence

ORD record
ord-604de3edfa864502a15b78aa83fd5629
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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