Diisopropylethylamine → benzyl 2-[3-({[4-fluoro-2-(methylsulfonyl)benzyl]amino}carbonyl)-4-hydroxy-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl(methyl)carbamate

HRID 1179318Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]([CH3:30])[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[C:17]([OH:24])=[C:16]([C:25](OC)=[O:26])[C:15]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl-].[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][NH3+:49])=[C:44]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:43]=1>CO>[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][NH:49][C:25]([C:16]2[C:15](=[O:29])[N:14]([CH2:13][CH2:12][N:11]([CH3:30])[C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:23]3[C:18]([C:17]=2[OH:24])=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:26])=[C:44]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:43]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methyl 1-{2-[[(benzyloxy)carbonyl](methyl)amino]ethyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.5 g, 1.21 mmol) in MeOH (6 mL) was treated with Hunig's base (0.33 mL, 1.82 mmol) and 1-[4-fluoro-2-(methylsulfonyl)phenyl]methanaminium chloride (0.35 g, 1.46 mmol) and heated in a sealed reaction vessel at 80 degrees C. After overnight, an additional 0.5 equivalents of the amine and 1.5 equivalents of Hunig's base was added and the reaction heated until HPLC showed the starting material gone. The reaction was cooled and the solids that percipitated were collected by filtration to give pure product.

Workup

temperaturethe reaction heated until HPLC
temperatureThe reaction was cooled
filtrationthe solids that percipitated were collected by filtration
customto give pure product

Sources & evidence

ORD record: ord-4aec81a40a8141f887e11c34eb4c1a55
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279487B2

Reaction notes

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