関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid | HCID 2733865 | — |
| 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-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine | HCID 66859070 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | Ammonium Acetate | HCID 517165 | — |
| 生成物 | Hexahydro-2,5-methano-pentalene-3a-carboxylic acid [5-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene]-amide | HCID 24890079 | — |
反応手順
A mixture of the product of Example 43A (342 mg, 1.29 mmol), hexahydro-2,5-methano-pentalene-3a-carboxylic acid (256 mg, 1.54 mmol), HATU (737 mg, 1.24 mmol) and triethylamine (1.08 mL, 7.74 mmol) in 20 mL of DMF was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes to afford the title compound: 1H NMR (500 MHz, DMSO-d6l) δ 1.51-1.61 (m, 4 H) 1.64-1.75 (m, 4 H) 2.06 (d, J=9.2 Hz, 2 H) 2.22-2.27 (m, 2 H) 2.51-253 (m, 1 H) 3.25 (s, 3 H) 3.67 (t, J=5.3 Hz, 2 H) 3.95 (s, 2 H) 4.23 (t, J=5.2 Hz, 2 H) 7.15 (t, J=8.8 Hz, 2 H) 7.23 (s, 1 H) 7.29 (dd, J=8.4, 5.6 Hz, 2 H); MS (DCI/NH3) m/z 415 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US07875639B2 |
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| 出典データセット | uspto-grants-2011_01 |
|---|
| ORD ID | ord-b41986b26a734960a50032a3735f249e |
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| 出典メモ | uspto-grants-2011_01 |
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