Triethylamine → N-[1-(6-Methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl]-N-methyl-acetamide

HRID 1992514Notes

Reaction equation

[C:1]([N:4]([CH:6]1[CH2:10][CH2:9][NH:8][CH2:7]1)[CH3:5])(=[O:3])[CH3:2].[CH3:11][O:12][C:13]1[N:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2OS(C(F)(F)F)(=O)=O.C(N(CC)CC)C>O1CCOCC1>[CH3:11][O:12][C:13]1[N:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[C:16]2[N:8]1[CH2:9][CH2:10][CH:6]([N:4]([CH3:5])[C:1](=[O:3])[CH3:2])[CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

3-(N-acetyl-N-methylamino)pyrrolidine (1.00 g, 7.0 mmol) was dissolved in dioxane (15 mL) and treated with 1,1,1-Trifluoro-methanesulfonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (1.67 g, 5.4 mmol) and triethylamine (0.98 mL, 7.0 mmol). After stirring at 50° C. overnight the reaction mixture was cooled, concentrated to dryness and purified via column chromatography (silica, 2% MeOH in chloroform) to afford the title compound as an off-white solid (1.72 g, quantitive): LC-MS m/z 301 (M+H)+

Workup

temperaturewas cooled
concentrationconcentrated to dryness
custompurified via column chromatography (silica, 2% MeOH in chloroform)

Sources & evidence

ORD record: ord-bb602f5cb0114fc5a762f9076aafbea9
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648984B2

Reaction notes

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