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1-Hydroxybenzotriazole → 3-iodo-4-methyl-N-(1-(pyridin-2-yl)cyclopropyl)benzamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 3-Iodo-4-methylbenzoic acid | HCID 621640 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | 1-(Pyridin-2-yl)cyclopropanamine | HCID 11105409 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 3-iodo-4-methyl-N-(1-(pyridin-2-yl)cyclopropyl)benzamide | HCID 67217666 | — |
反応手順
3-Iodo-4-methylbenzoic acid (2.5 g, 9.5 mmol, 1 eq), 1-(pyridin-2-yl)cyclopropanamine (1.41 g, 10.4 mmol, 1.1 eq), EDCI.HCl (2.1 g, 11.4 mmol, 1.2 eq), HOBT (1.5 g, 11.4 mmol, 1.2 eq) and DIPEA (4.9 ml, 28.62 mmol, 3 eq) were dissolved in DCM and the above solution was stirred at room temperature for 18 h. Water was added and product was extracted with DCM. The organic layer was concentrated and the crude product crystallized using dichloromethane and hexane. Yield: 2.3 g (55%). 1HNMR (400 MHz, DMSO-d6): δ 1.26 (m, 2H), 1.53 (m, 2H), 2.43 (s, 3H), 7.13 (m, 1H), 7.29 (d, J=8.00 Hz, 1H), 7.44 (d, 1H), 7.67 (t, J=3.46 Hz, 1H), 7.87 (d, J=3.24 Hz, 1H), 8.38 (s, 1H), 8.44 (d, J=1.10 Hz, 1H), 9.29 (s, 1H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08293909B2 |
| 出典データセット | uspto-grants-2012_10 |
| ORD ID | ord-6405fd1cc2ae4543ba906786ef7a7aad |
| 出典メモ | uspto-grants-2012_10 |