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[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[C:7]2[C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([C:18]([O:20]C)=[O:19])=[CH:13][CH:14]=3)[O:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.[NH:25]([C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)[NH2:26]>>[C:31]([C:30]1[CH:33]=[CH:34][C:27]([N:25]2[CH:6]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=3)[CH:7]3[CH2:8][O:9][C:10]4[CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=[CH:14][C:15]=4[C:16]3=[N:26]2)=[CH:28][CH:29]=1)#[N:32]참가 물질
실험 절차
The title compound was prepared from methyl 3-(4-fluorobenzylidene)-4-oxochroman-7-carboxylate; Preparation 30 (155 mg, 0.50 mmol) and 4-hydrazinylbenzonitrile hydrochloride (Aldrich) (127 mg, 0.75 mmol) according to Method B and Method C. The crude product was purified by reverse-phase HPLC (acetonitrile/water/0.05% trifluoroacetic acid) to give 2-(4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid (52 mg, 0.13, 25% yield). The title compound was largely present as (±)-(3SR,3aSR)-2-(4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.17 (dd, J=12.89, 10.47 Hz, 1H), 4.19-4.32 (m, 1H), 4.39 (dd, J=10.47, 5.91 Hz, 1H), 5.97 (d, J=11.55 Hz, 1H), 6.93-7.27 (m, 6H), 7.40 (d, J=1.61 Hz, 1H), 7.57-7.63 (m, 3H), 7.99 (d, J=8.06 Hz, 1H), 13.18 (s, 1H). ES-MS m/z 414 (M+H).
후처리
- customThe crude product was purified by reverse-phase HPLC (acetonitrile/water/0.05% trifluoroacetic acid)
출처 및 근거
- ORD 기록
- ord-3281c50a9bf249409f8a9741ac95fa52
- 출처 데이터셋
- uspto-grants-2010_08
- 특허 번호
- US07781428B2
연결된 노트
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