Hydrochloric Acid → 2-((6-Oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-9-ylamino)methyl)benzamide

HRID 1029299Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:26].[Na+].Cl>O1CCOCC1>[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]([NH2:21])=[O:26])=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

Conditions

Temperature: 150 °C

Procedure

462 (51 mg, 0.16 mmol) and NaOH (1M, aqueous, 2 mL) were suspended in dioxane (2 mL), and stirred for 30 minutes at 150° C. The reaction mixture was acidified with HCl (2M in diethyl ether, 1.6 mL), concentrated, and purified via prep-LC-MS to provide 481 (4 mg, 7% yield) as a white powder. LC-MS (M+H=345, obsd.=345). 1H NMR (400 MHz, DMSO-D6) δ 8.56 (d, J=7.9, 1H), 8.43 (d, J=3.1, 1H), 8.05 (d, J=8.6, 1H), 7.94 (d, J=6.7, 1H), 7.45 (s, 1H), 7.25 (m, 3H), 6.92 (d, J=8.6, 1H), 6.66 (s, 1H), 5.98 (s, 2H).

Workup

concentrationconcentrated
custompurified via prep-LC-MS

Sources & evidence

ORD record: ord-3aff56d8b96a43f09101a20dccb11a56
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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