ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate → N,N-Dibutyl-4-chloro-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole-3-carboxamide

HRID 528930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528930
[Cl:1]C1C(C(OCC)=O)=NNC=1C.[CH2:13]([N:17]([CH2:34][CH2:35][CH2:36][CH3:37])[C:18]([C:20]1[CH:24]=[C:23]([CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[NH:22][N:21]=1)=[O:19])[CH2:14][CH2:15][CH3:16]>>[CH2:34]([N:17]([CH2:13][CH2:14][CH2:15][CH3:16])[C:18]([C:20]1[C:24]([Cl:1])=[C:23]([CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[NH:22][N:21]=1)=[O:19])[CH2:35][CH2:36][CH3:37]

Komponenten

3

Edukt 2

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylateHCID 71062468N,N-Dibutyl-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole-3-carboxamide

Produkt 1

HCID 71060785N,N-Dibutyl-4-chloro-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole-3-carboxamideAusbeute 79 %

Versuchsvorschrift

Following a procedure analogous to that for the synthesis of Intermediate 1A, N,N-dibutyl-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole-3-carboxamide (355 mg, 1.01 mmol) was converted to the title compound (327 mg, 79%). 1H NMR (CD3OD) δ 4.60 (t, J=3.4 Hz, 1H), 3.94 (td, J=9.7, 6.5 Hz, 1H), 3.79-3.61 (m, 2 H), 3.59-3.41 (m, 3H), 3.39-3.25 (m, 2H), 3.04-2.91 (m, 2H), 1.87-1.34 (m, 12H), 1.27-1.09 (m, 2H), 0.99 (t, J=7.3 Hz, 3H), 0.81 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 386.3 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-f9489007a9a14e6ea2d64e9cbc4888ef
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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