Triethylamine → HCID 68861896, compound

HRID 2099123Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11](Cl)=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:19][CH3:20])[CH:7]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:28]([O:32][C:33](=[O:38])[NH:34][CH2:35][CH2:36][NH2:37])([CH3:31])([CH3:30])[CH3:29]>C1COCC1.CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([NH:37][CH2:36][CH2:35][NH:34][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:38])=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:19][CH3:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (2.20 g, 7.37 mmol) in THF (20 mL) and MeCN (20 mL) was treated with triethylamine (3.07 mL, 22.0 mmol), followed by (2-amino-ethyl)-carbamic acid tert-butyl ester (1.41 g, 8.80 mmol) and the mixture heated to 70° C. After 26 h (2-amino-ethyl)-carbamic acid tert-butyl ester (300 mg, 1.87 mmol) was added. After a further 15 h the heating was stopped and the solvent removed in vacuo. The residue was taken up in ethyl acetate, washed with water, dried filtered, and concentrated in vacuo to give a residue which was purified by chromatography (silica gel, 30-100% ethyl acetate in petroleum ether (b.p. 40-60° C.)) to give the title compound (2.89 g); ESMS m/z 423 [M+H]+.

Workup

customthe solvent removed in vacuo
washwashed with water
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customto give a residue which
customwas purified by chromatography (silica gel, 30-100% ethyl acetate in petroleum ether (b.p. 40-60° C.))

Sources & evidence

ORD record: ord-2580e9effe0b4501a55e9f1194661e58
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569550B2

Reaction notes

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