反応式
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.O.[OH-].[K+].[CH:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)([CH3:16])[CH3:15]>C(O)C>[CH:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:7]3[N:8]=[CH:9][NH:10][C:6]=3[CH2:5][CH2:4][NH:3]2)=[CH:19][CH:18]=1)([CH3:16])[CH3:15]参加物
実験手順
A mixture of histamine dihydrochloride (1.85 g, 10.0 mmol), water (10 mL), potassium hydroxide (1.72 g, 30.0 mmol), ethanol (25 mL) and 4-isopropylbenzaldehyde (1.62 g, 10.91 mmol) was heated to reflux for 1.5 h. Ethanol was evaporated and the residue was diluted with water (40 mL). Extraction (5×25 mL DCM), washing of the combined extracts (2×50 mL brine) and drying (MgSO4) yielded 2.29 g (87%) of crude 4-(4-isopropylphenyl)-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine, which was used for the next synthetic step without further purification. This amine (0.48 g, 1.99 mmol) was dissolved in DCM (5 mL) and added to a 30 min old mixture of 3-(4-fluorophenyl)propionic acid (0.31 g, 1.84 mmol), HOBt (0.27 g, 1.20 mmol) and EDC (0.42 g, 12.19 mmol) in DCM (10 mL). After 18 h the mixture was washed with water (50 mL), dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution with DCM/methanol). 0.24 g (33%) of the title amide was obtained.
後処理
- temperaturewas heated
- temperatureto reflux for 1.5 h
- customEthanol was evaporated
- additionthe residue was diluted with water (40 mL)
- extractionExtraction (5×25 mL DCM)
- washwashing of the combined extracts (2×50 mL brine)
- dry with materialdrying (MgSO4)
出典と根拠
- ORDレコード
- ord-41a7616a709e43fe9607f9524313d021
- 出典データセット
- uspto-grants-2005_06
- 特許番号
- US06908926B1
関連ノート
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