Benzylamine → N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine

HRID 2192971

Reaction equation

FC(F)(F)S(O[C:7]1[C:16]2[CH:17]=[CH:18][N:19]=[CH:20][C:15]=2[C:14]2[C:9](=[CH:10][CH:11]=[N:12][C:13]=2[O:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:8]=1)(=O)=O.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:28]([NH:35][C:7]1[C:16]2[CH:17]=[CH:18][N:19]=[CH:20][C:15]=2[C:14]2[C:9](=[CH:10][CH:11]=[N:12][C:13]=2[O:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:8]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate (127 mg, 0.253 mmol) in THF (2531 μl), benzylamine (111 μl, 1.013 mmol) was added. The reaction mixture was heated at 80° C. for 1 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. Aqueous sodium hydrogen carbonate (saturated) was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine as a brown oil. LRMS (APCI) calc'd for (C22H23N4O) [M+H]+, 359.2; found 359.1.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-87ee2705a0a540178279a90bb600c4d5
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329722B2

Linked notes

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