Sodium Iodide → HCID 86665049, compound

HRID 1047167Notes

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]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[I-].[Na+].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]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[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 (S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate hydrochloride (Intermediate 62, 1 g, 2.4 mmol, 1 equiv.) in acetonitrile (6 mL) was added 4-(2-chloroethyl)morpholine hydrochloride (447 mg, 2.4 mmol, 1 equiv.) followed by sodium iodide (360 mg, 2.4 mmol, 1 equiv.) and potassium carbonate (1.66 g, 12 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 precipitates were removed, and the filtrate was concentrated to provide (S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate as a solid (501.3 mg, 43%). Calcd for C22H29BrN4O4 [M+H]+: 495.07.

Workup

temperatureThe reaction was cooled to room temperature
customThe precipitates were removed
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-1464187319f947cd8fbda667023c56b6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569484B2

Reaction notes

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