4-Hydrazinyl-2-methylbenzonitrile hydrochloride → HCID 59429310、化合物

HRID 505740

反応式

HRID 505740 の反応式
[CH:1]1([CH:4]=[C:5]2[C:14](=O)[C:13]3[C:8](=[CH:9][C:10]([C:16]([O:18]C)=[O:17])=[CH:11][CH:12]=3)[O:7][CH2:6]2)[CH2:3][CH2:2]1.Cl.[NH:21]([C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([CH3:31])[CH:24]=1)[NH2:22]>>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([N:21]2[CH:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]3[CH2:6][O:7][C:8]4[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[CH:11]=[CH:12][C:13]=4[C:14]3=[N:22]2)=[CH:24][C:25]=1[CH3:31])#[N:28]

参加物

3

反応物 2

HCID 469150334-Hydrazinyl-2-methylbenzonitrile hydrochlorideHCID 66722637Methyl 3-(cyclopropylmethylene)-4-oxochroman-7-carboxylate

生成物 1

HCID 59429310HCID 59429310、化合物

実験手順

The title compound was prepared from methyl 3-(cyclopropylmethylene)-4-oxochroman-7-carboxylate (Preparation 33), and 4-hydrazinyl-2-methylbenzonitrile hydrochloride (Preparation 2) according to Method B and Method C. The crude product was purified by reverse-phase HPLC (65 to 85% acetonitrile/water/0.05% trifluoroacetic acid) to give the title compound (yellow solid, 23 mg). The title compound was largely present as (±)-(3RS,3aSR)-2-(4-cyano-3-methylphenyl)-3-cyclopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.11 (br. s., 1H), 7.94 (d, J=7.8 Hz, 1H), 7.58 (dd, J=8.2, 1.6 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 7.47 (d, J=1.6 Hz, 1H), 7.23 (d, J=1.6 Hz, 1H), 7.11 (dd, J=8.6, 2.0 Hz, 1H), 4.84 (dd, J=10.5, 5.9 Hz, 1H), 4.45 (dd, J=12.9, 10.5 Hz, 1H), 4.31 (t, J=10.0 Hz, 1H), 3.89 (ddd, J=13.0, 9.9, 5.7 Hz, 1H), 2.42 (s, 3H), 0.71-0.81 (m, 1H), 0.62-0.70 (m, 1H), 0.49-0.58 (m, 1H), 0.35-0.43 (m, 1H), 0.17-0.24 (m, 1H). ES-MS m/z 374 (M+H).

後処理

  1. customThe crude product was purified by reverse-phase HPLC (65 to 85% acetonitrile/water/0.05% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-924c7c226afc4f84bea17ff5c4a75588
出典データセット
uspto-grants-2010_08
特許番号
US07781428B2

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