Potassium Carbonate → HCID 86665053, compound

HRID 1047169Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][N:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24].Cl.Cl[CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][N:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24]

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of (5)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate hydrochloride (Intermediate 62, 610 mg, 1.46 mmol, 1 equiv.) in acetonitrile (4 mL) was added 2-chloro-N,N-diethylethanamine hydrochloride (252 mg, 1.46 mmol, 1 equiv.) followed by potassium carbonate (1 g, 7.32 mmol, 5 equiv.). This was stirred in the microwave at 120° C. for 30 min. The reaction was cooled to room temperature and diluted with ethyl acetate. The precipitate was discarded, and the filtrate was concentrated to provide (S)-ethyl 6-bromo-1-(1-(2-(diethylamino)ethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate as a solid (mg, %).

Workup

temperatureThe reaction was cooled to room temperature
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-a5a71f7ff9be43958a09771f294f73b4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569484B2

Reaction notes

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