関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 3-Aminopyridine | HCID 10009 | — |
| 反応物 | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| 反応物 | 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid | HCID 71280096 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide | HCID 71279692 | 26% |
反応手順
A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.07 g, 0.3 mmol), pyridin-3-amine (0.05 g, 0.53 mmol), EDCI (0.057 g, 0.3 mmol), DMAP (0.037 g, 0.3 mmol), and DIPEA (0.163 g, 1.26 mmol) in 10 mL of DMF were stirred at room temperature for 5 hours. Then HATU (0.114 g, 0.3 mmol) was added, the final reaction mixture was stirred for additional. The solvent was removed under reduced pressure at 70° C. The residue was triturated with water, EtOAc and DMSO successively then decanted and dried to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.022 g, 26%) as a white solid. MS: (M+H)+=404; 1H NMR (300 MHz, DMSO): δ 10.20 (s, 1H), 9.09 (s, 1H), 8.90 (s, 1H), 8.63 (s, 1H), 8.54 (d, 1H, J=8.7 Hz), 8.34 (d, 1H, J=4.5 Hz), 8.26 (d, 1H, J=8.7 Hz), 7.98 (s, 1H), 7.47 (dd, 1H, J=8.4, 4.8 Hz), 7.22 (d, 1H, J=8.4 Hz), 4.17 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08658646B2 |
|---|
| 出典データセット | uspto-grants-2014_02 |
|---|
| ORD ID | ord-8c16b8cd204f49039518315217b668c6 |
|---|
| 出典メモ | uspto-grants-2014_02 |
|---|
