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Sodium Bicarbonate → N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-5-formyl-N-methylthiophene-2-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | 5-Formyl-2-thiophenecarboxylic Acid | HCID 818882 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | 2-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamide | HCID 86663419 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-5-formyl-N-methylthiophene-2-carboxamide | HCID 86663421 | 100% |
反応手順
The compound (73 mg, 0.157 mmol) obtained in Example 1k was dissolved in methylene chloride (3 mL), 5-formyl-thiophene-2-carboxylic acid (40 mg, 0.257 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (89 mg, 0.464 mmol) were added, and the mixture was stirred at room temperature for 1.5 hours. A saturated aqueous sodium hydrogencarbonate solution was added, and then the mixture was extracted with ethyl acetate (×3) and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1→20:1, v/v) to give the title compound (144 mg; yield, 61%) as a white solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08476253B2 |
| 出典データセット | uspto-grants-2013_07 |
| ORD ID | ord-70f5ea9348d14a99891decaf0928fed0 |
| 出典メモ | uspto-grants-2013_07 |