4-Hydrazinyl-2-methylbenzonitrile hydrochloride → 2-(4-cyano-3-methylphenyl)-3-cyclopentenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid

HRID 505730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505730
[C:1]1([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([O:19]C)=[O:18])[CH:11]=[CH:10][C:9]=3[C:8]2=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.[NH:23]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([CH3:33])[CH:26]=1)[NH2:24]>>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:23]2[CH:6]([C:1]3[CH2:5][CH2:4][CH2:3][CH:2]=3)[CH:7]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([C:17]([OH:19])=[O:18])=[CH:13][C:14]=4[CH2:15][CH2:16]3)=[N:24]2)=[CH:26][C:27]=1[CH3:33])#[N:30]

Komponenten

3

Edukt 2

HCID 469150334-Hydrazinyl-2-methylbenzonitrile hydrochlorideHCID 66722894Methyl 6-(cyclopent-1-en-1-ylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Produkt 1

HCID 594294362-(4-cyano-3-methylphenyl)-3-cyclopentenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid

Versuchsvorschrift

The title compound was injustices prepared from methyl 6-(cyclopent-1-en-1-ylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate; Preparation 24 and 4-hydrazinyl-2-methylbenzonitrile hydrochloride; Preparation 2 according to Method B and Method C. The title compound was largely present as (±)-(3RS,3aRS)-2-(4-cyano-3-methylphenyl)-3-cyclopentenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.85 (m, 4H), 1.88-2.12 (m, 2H), 2.18 (s, 2H), 2.38 (s, 3H), 2.99 (d, J=4.0 Hz, 2H), 3.55-3.75 (m, 1H), 5.39 (d, J=10.7 Hz, 1H), 5.62 (s, 1H), 6.86 (br. s., 1H), 7.13 (br. s., 1H), 7.52 (d, J=8.6 Hz, 1H), 7.69-7.89 (m, 2H), 8.03 (d, J=7.8 Hz, 1H), 12.99 (s, 1H); ES-MS m/z 398 (M+H).

Aufarbeitung

  1. customPreparation 2 according to Method B and Method C

Quellen und Nachweise

ORD-Eintrag
ord-09a48964380b4571aec8185cfeaa1b0e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781428B2

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