関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylamine | HCID 674 | — |
| 反応物 | 4-Methylmorpholine | HCID 7972 | — |
| 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 | 5-Carboxy-2-methoxybenzeneboronic acid | HCID 42614541 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 5-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid | HCID 57556078 | 45.4% |
反応手順
To a solution of 700 mg (3.57 mmol) 3-borono-4-methoxybenzoic acid in 23 ml DMF, 3.6 ml (7.14 mmol) dimethylamine, 1.5 g (3.93 mmol) HATU and 1.57 ml (14.29 mmol) NMM were added and stirred at RT for 2 hours. The reaction mixture was extracted with EtOAc and water. The organic phase was dried over Na2SO4, filtered and evaporated. The residue was purified by preparative HPLC (Prep. HPLC method 1, gradient: 15-30% in 16 minutes). The fractions containing product were combined and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated to afford 361 mg (1.619 mmol, 45.3% yield) of the title compound as a colorless solid. LCMS: (M+H)=224; tR=0.54 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) δ ppm 7.56 (m, 1H) 7.44 (dd, 1H) 6.99 (d, 1H) 3.81 (s, 3H) 2.93 (s, 6H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09403827B2 |
|---|
| 出典データセット | uspto-grants-2016_08 |
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| ORD ID | ord-4c438aa47c594e108e8b5422e3718a58 |
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| 出典メモ | uspto-grants-2016_08 |
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