関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 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 | 3-Amino-5-chloro-2-nitrobenzoic acid | HCID 10727479 | — |
| 反応物 | 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium | HCID 86621144 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Methyl 3-amino-5-chloro-2-nitrobenzoate | HCID 12165619 | 64% |
反応手順
A mixture of 3-amino-5-chloro-2-nitrobenzoic acid (43.2 g) and HATU (2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium, commercially available) (76 g) in MeOH (81 mL), Et3N (83 mL) and THF (300 mL) was stirred at room temperature for 3 h. When TLC showed no starting material, the solvent was removed in-vacuo and the residue was then diluted with EtOAc (2 L). It was then washed with brine (1 L×3) and dried over anhydrous Na2SO4, filtered and concentrated in-vacuo. The residue was then purified by silica gel chromatography eluted with EtOAc:petroleum ether=1:8 to afford the desired product as a yellow solid (29.5 g, yield 64%). 1H NMR (300 MHz, CDCl3): δ ppm 3.90 (s, 3H, s), 5.85 (br s, 2H), 6.80 (d, 1H, J=2.4 Hz), 6.90 (d, 1H, J=2.4 Hz); LC-MS: m/e=231 [M+1]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08541411B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
|---|
| ORD ID | ord-8b28922414d3416db20db88695315086 |
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| 出典メモ | uspto-grants-2013_09 |
|---|
