4-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide → Ethyl 4-(4-bromo-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate
Reaktionsgleichung
[Br:1][C:2]1[C:3]([C:8]([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])=[N:4][NH:5][C:6]=1[CH3:7].F[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=1[C:31]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34]1)=[O:32]>>[Br:1][C:2]1[C:3]([C:8](=[O:9])[N:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH2:17][CH3:18])=[N:4][N:5]([C:20]2[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[C:6]=1[CH3:7]Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
Following a procedure analogous to that for the synthesis of Intermediate 1E, 4-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide (646 mg, 2.04 mmol) and ethyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (Intermediate 1D, 1.07 g, 3.27 mmol) were converted to the title compound (660 mg, 48%). 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 8.24-8.19 (m, 1H), 8.14-8.10 (m, 1H), 7.45-7.39 (m, 1H), 7.25-7.09 (m, 3.5H), 6.88 (d, J=7.3 Hz, 0.5H), 4.78 (d, J=8.8 Hz, 1H), 4.49-4.36 (m, 3H), 3.71-2.69 (m, 8H), 2.32 (s, 2H), 2.28 (s, 1H), 1.54-1.27 (m, 8.5H), 1.11 (d, J=7.7 Hz, 2H), 0.92 (q, J=7.2 Hz, 3.5H), 0.79 (t, J=8.0 Hz, 3H); MS(ESI+) m/z 625.3 (M+H)+.
Quellen und Nachweise
- ORD-Eintrag
- ord-fc9f3571de2c44caa571fca1779e3bcb
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09346795B2
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