Reaktionsgleichung
[CH3:1][CH:2]([CH3:19])[CH:3]=[C:4]1[C:13](=O)[C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17]C)=[O:16])=[CH:10][CH:11]=2)[O:6][CH2:5]1.Cl.[Cl:21][C:22]1[CH:29]=[C:28]([NH:30][NH2:31])[CH:27]=[CH:26][C:23]=1[C:24]#[N:25].O1CCCC1>>[Cl:21][C:22]1[CH:29]=[C:28]([N:30]2[CH:3]([CH:2]([CH3:19])[CH3:1])[CH:4]3[CH2:5][O:6][C:7]4[CH:8]=[C:9]([C:15]([OH:17])=[O:16])[CH:10]=[CH:11][C:12]=4[C:13]3=[N:31]2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]Komponenten
Versuchsvorschrift
The title compound was prepared from methyl 3-(2-methylpropylidene)-4-oxochroman-7-carboxylate; Preparation 32 (260 mg, 1.0 mmol) and 2-chloro-4-hydrazinylbenzonitrile hydrochloride; Preparation 1 (306 mg, 1.5 mmol) according to Method B and Method C. The crude product was purified by reverse-phase HPLC (30 to 95% acetonitrile/water/0.05% trifluoroacetic acid) followed by flash chromatrography (0 to 20% methanol/ethyl acetate) to give 2-(3-chloro-4-cyanophenyl)-3-isopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid (yellow solid, 18.4 mg). The title compound was largely present as (±)-(3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-isopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.10 (br. s., 1H), 7.95 (d, J=7.8 Hz, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.58 (dd, J=8.2, 1.6 Hz, 1H), 7.47 (d, J=1.2 Hz, 1H), 7.42 (d, J=2.3 Hz, 1H), 7.19 (dd, J=9.0, 1.6 Hz, 1H), 4.77-4.88 (m, 2H), 4.41 (dd, J=13.3, 10.5 Hz, 1H), 4.00-4.09 (m, 1H), 2.04-2.16 (m, 1H), 0.83 (d, J=7.0 Hz, 3H), 0.82 (d, J=7.0 Hz, 3H).
Aufarbeitung
- customThe crude product was purified by reverse-phase HPLC (30 to 95% acetonitrile/water/0.05% trifluoroacetic acid)
Quellen und Nachweise
- ORD-Eintrag
- ord-d4460f1709dd45cba2f6a6baf6e6503a
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07781428B2
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