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Diisopropylethylamine → 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 4-Amino-1,2,5-thiadiazole-3-carboxylic acid | HCID 251763 | — |
| 反応物 | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| 反応物 | 3-Bromo-4-fluoroaniline | HCID 2779286 | — |
| 溶媒 | Hydrochloric Acid | HCID 313 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Sodium chloride; water | HCID 57417360 | — |
| 生成物 | 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carboxamide | HCID 58558244 | 76.8% |
反応手順
A solution of 4-amino-1,2,5-thiadiazole-3-carboxylic acid (250 mg, 1.7 mmol) and 3-bromo-4-fluoroaniline (393 mg, 2.1 mmol) in N,N-dimethylformamide (5 mL) was treated with O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (784 mg, 2.1 mmol) followed by N,N-diisopropylethylamine (0.36 mL, 2.1 mmol) and stirred for 16 h. The reaction mixture was diluted with brine (50 mL) and 0.1 N HCl (100 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated. Purification of the crude reaction mixture on silica gel gave the desired product (414 mg, 76%). LCMS for C9H7BrFN4OS(M+H)+: m/z=316.9, 318.8.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08846726B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-69346c588eb44b14954f090f58745a3b |
| 出典メモ | uspto-grants-2014_09 |