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Cesium carbonate → 1-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Isoquinolin-3-Amine | HCID 311869 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | 1-(2-Chloropyridin-4-ylmethyl)-4-acetylpiperazine | HCID 58285182 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 1-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone | HCID 44612470 | — |
反応手順
1-(2-Chloropyridin-4-ylmethyl)-4-acetylpiperazine (1.0 equiv) (Preparation B-15) was mixed with 3-aminoisoquinoline (1.0 equiv), Pd2(dba)3(0.1 equiv), xantphos (0.15 equiv), and Cs2CO3 (1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound was obtained as a yellow solid (50 mg, yield 48%). 1H NMR (CDCl3, 300 MHz) δ: 2.10 (s, 3H, Ac), 2.47 (t, J=4.1 Hz, 4H, PyCH2NCH2CH2), 3.58 (dt, J=4.8 Hz, 50.7 Hz, 4H, NCH2CO), 3.60 (s, 2H, pyridylCH2), 6.86-8.99 (m, 9H, isoquinolyl+pyridyl).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08461339B2 |
| 出典データセット | uspto-grants-2013_06 |
| ORD ID | ord-4e4cae14340f4d6fb08ae527b6bbb156 |
| 出典メモ | uspto-grants-2013_06 |