참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Thionyl Chloride | HCID 24386 | — |
| 반응물 | 2,3-Dihydro-1-benzofuran-7-carboxylic acid | HCID 2795014 | — |
| 반응물 | 2,3-Dihydro-1-benzofuran-7-carbonyl chloride | HCID 2795016 | — |
| 반응물 | 3-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine | HCID 66851723 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | HCID 178495793 | HCID 178495793 | 34% |
반응 단계
The 2,3-dihydrobenzofuran-7-carboxylic acid (TCI-US, 0.25 g, 1.4 mmol) was converted to 2,3-dihydrobenzofuran-7-carbonyl chloride with 5 mL of thionyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and the freshly prepared 2,3-dihydrobenzofuran-7-carbonyl chloride in 30 mL THF were processed as in Example 134B. Purification of the crude material via recrystallization with 50% hexanes:EtOAc gave the title compound (0.12 g, 0.36 mmol, 34% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.25 (s, 3H), 2.30 (s, 3H), 3.22 (t, J=8.8 Hz, 2H), 3.31 (s, 3H), 3.81 (t, J=5.3 Hz, 2H), 4.44 (t, J=5.3 Hz, 2H), 4.64 (t, J=8.8 Hz, 2H), 6.86 (t, J=7.5 Hz, 1H), 7.32 (dd, J=7.3, 1.2 Hz, 1H), 7.93 (dd, J=8.0, 0.8 Hz, 1H); MS (DCI/NH3) m/z 333 (M+H)+; Anal. calculated for C17H20N2O3S.0.1H2O: C, 61.09; H, 6.09; N, 8.38. Found: C, 60.99; H, 5.91; N, 8.25.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08841334B2 |
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| 출처 데이터셋 | uspto-grants-2014_09 |
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| ORD ID | ord-c92914153a104907ae9077d9926d5e07 |
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| 출처 메모 | uspto-grants-2014_09 |
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