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Hydrochloric Acid → 3-Aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride

HRID 1887824
Notes
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Reaction equation

HRID 1887824 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[C:12]([C:13](=[O:19])[C:14]=1[CH2:15][N:16]=[N+]=[N-])=[CH:11][CH:10]=[C:9]([C:20]([F:23])([F:22])[F:21])[N:8]=2)=[O:4].[ClH:30].C(OCC)(=O)C>O1CCOCC1.CO.[Pt](=O)=O>[ClH:30].[CH3:1][O:2][C:3]([C:5]1[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[C:12]([C:13](=[O:19])[C:14]=1[CH2:15][NH2:16])=[CH:11][CH:10]=[C:9]([C:20]([F:21])([F:23])[F:22])[N:8]=2)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 712083753-Azidomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

Product 1

HCID 712084273-Aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride

Reagents, catalysts & solvents 3

HCID 345198
Adams' catalyst
Catalyst
HCID 887MethanolSolvent
HCID 312751,4-DioxaneSolvent

Procedure

In a 100 mL pear-shaped flask, 3-azidomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (490 mg, 1.21 mmol), platinum (IV) oxide (100 mg, 0.440 mmol) and a 4N HCl in 1,4-dioxane (2.4 g, 2 mL) were combined with ethyl acetate (12 mL) to give a brown suspension which was hydrogenated at atmospheric pressure at 25° C. for 11 hr. The reaction mixture was diluted with methanol (200 mL), stirred for 1 hr at room temperature, filtered through a small celite pad, and concentrated under vacuum to give 3-aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride (0.54 g, 107% crude yield) as a light brown solid. Material was used without any further purification. 1H NMR (DMSO-d6) δ ppm 8.93 (d, J=8.2 Hz, 1H) 8.21 (br. s., 2H) 8.04 (d, J=8.2 Hz, 1H) 6.80-7.72 (m, 4H) 3.88 (br. s., 2H) 3.54 (s, 3H). MS calcd. for C18H14F3N3O3 [(M+H)+] 378.0, obsd. 378.0, [(M+H-NH3)+] 361.0, obsd. 361.0, [(M+H-NH3+CH3CN)+] 402.0, obsd. 402.0.

Workup

  1. customto give a brown suspension which
  2. filtrationfiltered through a small celite pad
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-11c0ef7c7a7e43a6bbe9f83699e63779
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501732B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes