Hydrochloric Acid → N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

HRID 869501Notes

Reaction equation

HRID 869501 reaction equation
[CH:1]12[N:7]([C:8]3[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]4[C:26](=[O:27])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]=5[CH3:28])[NH:19][CH:18]=4)=[O:16])=[C:10]([CH3:29])[CH:9]=3)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[ClH:30].CCOCC>CO>[ClH:30].[CH:4]12[N:7]([C:8]3[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]4[C:26](=[O:27])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]=5[CH3:28])[NH:19][CH:18]=4)=[O:16])=[C:10]([CH3:29])[CH:9]=3)[CH:1]([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 45259022N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 67368807N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide was dissolved in methanol (2 mL) and treated with 2 M HCl in ether (295.3 μL of 2 M, 0.5906 mmol). The solution was evaporated to provide N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride. 1H NMR (400.0 MHz, DMSO-d6) δ 12.71 (s, 1H), 12.12 (s, 1H), 8.78 (s, 1H), 8.74 (s, 1H), 7.63-7.59 (m, 1H), 7.54 (d, J=8.3 Hz, 1H), 7.22 (d, J=7.1 Hz, 1H), 6.81 (s, 1H), 4.44 (s, 2H), 2.91 (s, 3H), 2.28 (s, 3H), 1.65 (d, J=7.2 Hz, 4H), 1.42 (d, J=6.8 Hz, 4H).

Workup

  1. customThe solution was evaporated

Sources & evidence

ORD record
ord-d22b834923bf4b6bb566ab534af7abfe
Source dataset
uspto-grants-2015_03
Patent number
US08969382B2

Reaction notes

Loading…