5-Chloro-2-fluorobenzoyl chloride → (S)-3-(5-chloro-2-fluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

HRID 242488

Reaktionsgleichung

Reaktionsgleichung von HRID 242488
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([NH:11][C:12]([N:14]1[C:18]2[CH2:19][CH2:20][O:21][CH2:22][C:17]=2[C:16](C2C=CC(F)=C(F)C=2)=[N:15]1)=[O:13])[C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([F:42])=[C:37]([CH:41]=1)C(Cl)=O>>[Cl:32][C:33]1[CH:41]=[CH:37][C:36]([F:42])=[C:35]([C:16]2[C:17]3[CH2:22][O:21][CH2:20][CH2:19][C:18]=3[N:14]([C:12]([NH:11][C@@H:6]([C:7]([CH3:8])([CH3:10])[CH3:9])[C:5]([NH:4][CH2:3][CH2:2][OH:1])=[O:31])=[O:13])[N:15]=2)[CH:34]=1

Komponenten

3

Edukt 2

HCID 27736045-Chloro-2-fluorobenzoyl chlorideHCID 46220523(S)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-3-(3,4-difluorophenyl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Produkt 1

HCID 46834984(S)-3-(5-chloro-2-fluorophenyl)-N-(1-(2-hydroxyethylamino)-3,3-dimethyl-1-oxobutan-2-yl)-6,7-dihydropyrano[4,3-c]pyrazole-1(4H)-carboxamide

Versuchsvorschrift

Compound 86 was prepared according to the procedure for the synthesis of compound 36 by replacing 3,4-difluorobenzoyl chloride with 5-chloro-2-fluorobenzoyl chloride. LCMS (+ESI) m/z=453.3 [M+H]+. 1H NMR (CDCl3) δ 7.81 (d, J=9.1 Hz, 1H), 7.60-7.62 (dd, J=2.7, 6.21 Hz, 1H), 7.27-7.32 (m, 1H), 7.07 (t, J=9.3 Hz, 1H), 6.56 (br, 1H), 4.57 (s 2H), 4.12 (d, J=9.2 Hz, 1H), 3.87 (t, J=5.6 Hz, 2H), 3.66 (s, 3H), 3.36-3.41 (m, 2H), 3.08-3.12 (m, 2H), 1.03 (s, 9H). Purity: 97%.

Quellen und Nachweise

ORD-Eintrag
ord-abffb226c19846feb1924cd90fdac6b5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653127B2

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