Ethanol → 2-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid
反応式
[CH: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][CH2:2]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(O)C>>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:23]2[CH:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]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]参加物
実験手順
The title compound was prepared from Methyl 6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate; Preparation 18 (310.5 mg, 1.09 mmol) and 4-hydrazinyl-2-methylbenzonitrile hydrochloride; Preparation 2 (265 mg, 1.45 mmol) according to Method B and Method C (hydrolysis conducted at 60° C.). The crude precipitate was purified by reverse phase chromatography with 60-95% acetonitrile/water to give the title compound (yellow solid, 280 mg, 0.563 mmol, 64% yield). The title compound was largely present as (±)-(3SR,3aRS)-2-(4-cyano-3-methylphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.56 (m, 7H), 1.64-1.74 (m, 1H), 1.76-1.92 (m, J=12.89, 4.30 Hz, 1H), 2.01-2.14 (m, 1H), 2.18-2.29 (m, 1H), 2.41 (s, 3H), 2.81-2.96 (m, 1H), 3.04-3.14 (m, 1H), 3.51-3.63 (m, 1H), 4.89 (dd, J=9.67, 5.37 Hz, 1H), 7.09 (dd, J=8.59, 2.15 Hz, 1H), 7.22 (d, J=1.88 Hz, 1H), 7.52 (d, J=8.59 Hz, 1H), 7.82 (dd, J=8.19, 1.48 Hz, 1H), 7.85 (s, 1H), 8.07 (d, J=8.06 Hz, 1H), 13.01 (s, 1H). ES-MS m/z 400 (M+H).
後処理
- customaccording to Method B and Method C (hydrolysis conducted at 60° C.)
- customThe crude precipitate was purified by reverse phase chromatography with 60-95% acetonitrile/water
出典と根拠
- ORDレコード
- ord-b23594f5484847a3bcf648443f5f2915
- 出典データセット
- uspto-grants-2010_08
- 特許番号
- US07781428B2
反応ノート
読み込み中…