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1,1,1-Trimethoxybutane → 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,1,1-Trimethoxybutane | HCID 123512 | — |
| 反応物 | 4-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol | HCID 66919188 | — |
| 触媒 | Pyridinium chloride | HCID 10176127 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol | HCID 57515459 | 69.2% |
反応手順
Trimethylorthobutyrate (1.9 mL, 12.0 mmol) and pyridine hydrochloride (23 mg, 0.2 mmol) were added to a suspension of 4-[(3-amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the resulting solid was isolated by filtration to provide 2.26 g of 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07884207B2 |
| 出典データセット | uspto-grants-2011_02 |
| ORD ID | ord-c8fa798f809546f6a7b12674a69280f1 |
| 出典メモ | uspto-grants-2011_02 |