反応式
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:25]3[C:24](=O)[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][N:18]=2)=[O:16])=[CH:10][CH:9]=1)[CH3:2].C[N:30](C)[CH:31]=[CH:32][CH:33]=O.C([O-])(=O)C.[NH4+].[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:25]3[C:24]4[N:30]=[CH:31][CH:32]=[CH:33][C:23]=4[CH2:22][CH2:21][C:20]=3[NH:19][N:18]=2)=[O:16])=[CH:10][CH:9]=1)[CH3:2]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 100 °C
実験手順
A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide (192 mg, 0.50 mmol), 3-(dimethylamino)-acrolein 0.15 mL (1.50 mmol), ammonium acetate (384 mg, 5.00 mmol), and acetic acid (2.0 mL) is stirred under nitrogen at 100° C. for 16 h, poured into ice-cold 10% NaCl (20 mL), treated with 10 N NaOH to pH 12 and extracted with chloroform (30 mL). The extract is concentrated under reduced pressure and the residue is chromatographed on silica gel using chloroform-methanol-30% ammonium hydroxide (90:9:1, v/v/v) as an eluent to give pure 5,7-dihydro-6H-pyrazolo[3,4-h]quinoline-9-carboxylic acid [6-(3-diethylamino-propoxy)-pyridin-3-yl]-amide. 1H NMR (CDCl3) t, J=7.1 Hz, 6H), 1.96 (m, 2H), 2.57 (q, J=7.1 Hz, 4H), 2.65 (m, 2H), 3.10 (m, 4H), 4.33 (t, J=6.3 Hz, 2H), 6.80 (d, J=8.8 Hz, 1H), 7.21 (dd, J=7.7 and 4.9 Hz, 1H), 7.66 (d, J=7.7 Hz, 1H), 8.32 (dd, J=8.9 and 2.7 Hz, 1H), 8.44 (d, J=2.7 Hz, 1H), 8.47 (dd, J=4.9 and 1.1 Hz, 1H). MW 420.519; MS (M−H)− 419.
後処理
- extractionextracted with chloroform (30 mL)
- concentrationThe extract is concentrated under reduced pressure
- customthe residue is chromatographed on silica gel
出典と根拠
- ORDレコード
- ord-e47b6f89e57e447c89649d827c0bb06a
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06852730B2
関連ノート
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