Ethylamine → N-[3-(7-Ethylamino-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

HRID 270714Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1.[CH2:34]([NH2:36])[CH3:35]>C(O)CCC>[CH2:34]([NH:36][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1)[CH3:35]

Participants

Conditions

Temperature: 100 °C

Procedure

N-[3-(7-Chloro-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (50 mg, 0.106 mmol) is mixed with ethylamine (0.14 mL 70% in water, 2.2 mmol) in a sealed tube. 1 mL of n-butanol is added and the reaction is stirred at 100° C. for 16 hours. After cooling and removal of solvent under vacuum, the crude product is dissolved in DMSO and purified by reverse phase preparative HPLC to give the final product as white solid: 1H NMR 400 MHz (DMSO-d6) δ 10.47 (s, 1H), 8.48 (s, 1H), 8.29 (s, 1H), 8.25 (d, 1H, J=8.0 Hz), 7.96 (d, 1H, J=7.8 Hz), 7.78 (m, 2H), 7.66 (m, 2H), 7.26 (d, 1H, J=9.0 Hz), 6.46 (s, 1H), 3.57 (s, 3H), 3.39 (q, 2H, J=7.1 Hz), 2.13 (s, 3H), 1.22 (t, 3H, J=7.1 Hz); MS m/z 481.2 (M+1).

Workup

temperatureAfter cooling
customremoval of solvent under vacuum
dissolutionthe crude product is dissolved in DMSO
custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-47e090d1da184a7ab8dd83c1d45c1f6b
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449582B2

Reaction notes

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