Pipemidic Acid → 2-(4-{[(4-Trifluoromethylphenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

HRID 455942

Reaktionsgleichung

Reaktionsgleichung von HRID 455942
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[S:33])=[CH:27][CH:26]=1>>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[N:12]=[CH:13][C:8]4[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:2][CH3:1])[C:9]=4[N:10]=3)[CH2:15][CH2:16]2)=[S:33])=[CH:29][CH:30]=1

Komponenten

3

Edukt 2

HCID 4831Pipemidic AcidHCID 1371344-(Trifluoromethyl)phenyl isothiocyanate

Produkt 1

HCID 454841322-(4-{[(4-Trifluoromethylphenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

Versuchsvorschrift

Pipemidic acid (30 mg, 0.0989 mmol) and 4-trifluoromethylphenyl isothiocyanate (16.7 mg, 0.0824 mmol) were used. Purification on silica yielded compound 31 in Table 1, below (31 mg, 77%). 1H NMR (300 MHz, CDCl3) δ 9.34 (s, 1H), 8.69 (s, 1H), 7.65-7.57 (m, 2H), 7.51 (s, 1H), 7.37-7.31 (m, 2H), 4.34 (q, J=6.80 Hz, 2H), 4.27-3.97 (m, 8H), 1.49 (t, J=7.25, 7.25 Hz, 3H) ppm.

Aufarbeitung

  1. customPurification on silica yielded compound 31 in Table 1

Quellen und Nachweise

ORD-Eintrag
ord-289cf851df474d518cc0f27601d256ca
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497371B2

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