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2-Bromoethanol → 3-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2-Bromoethanol | HCID 10898 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | Ammonium Chloride | HCID 25517 | — |
| 反応物 | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| 反応物 | 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide | HCID 11245836 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamide | HCID 58088946 | 59.1% |
反応手順
To a solution of 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide (472 mg, 1.26 mmol) in THF (dry, 20 mL) at 0° C. was added of 2-bromoethanol (785 mg, 6.3 mmol), PPh3 (1.3g, 5.04 mmol) and diethyl azodicarboxylate (877 mg, 5.04 mmol) and the mixture was stirred at room temperature for 72 h. An aqueous solution of NH4Cl was added then the THF layer was isolated. The aqueous layer was extracted by EtOAc. The combined organic phase was washed by brine, purified by preparatory HPLC, to provide the product as a white solid (360 mg, 59%). HPLC (4 minute 10-90 gradient) tR 2.72 min; MS m/z 483.14/485.09 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07863314B2 |
| 出典データセット | uspto-grants-2011_01 |
| ORD ID | ord-31e3b9135a27465598f7f8657f9d85c5 |
| 出典メモ | uspto-grants-2011_01 |