참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid | HCID 2733865 | — |
| 반응물 | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| 반응물 | 5-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine | HCID 66859070 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | Ammonium Acetate | HCID 517165 | — |
| 생성물 | Hexahydro-2,5-methano-pentalene-3a-carboxylic acid [5-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene]-amide | HCID 24890079 | — |
반응 단계
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-d6) δ 1.51-1.61 (m, 4H) 1.64-1.75 (m, 4H) 2.06 (d, J=9.2 Hz, 2H) 2.22-2.27 (m, 2H) 2.51-2.53 (m, 1H) 3.25 (s, 3H) 3.67 (t, J=5.3 Hz, 2H) 3.95 (s, 2H) 4.23 (t, J=5.2 Hz, 2H) 7.15 (t, J=8.8 Hz, 2H) 7.23 (s, 1H) 7.29 (dd, J=8.4, 5.6 Hz, 2H); MS (DCI/NH3) m/z 415 (M+H)+.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09006275B2 |
|---|
| 출처 데이터셋 | uspto-grants-2015_04 |
|---|
| ORD ID | ord-5eb2b9baa88c464283358faed46f0019 |
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| 출처 메모 | uspto-grants-2015_04 |
|---|
