반응식
[CH:1]1([CH:4]=[C:5]2[C:14](=O)[C:13]3[C:8](=[CH:9][C:10]([C:16]([O:18]C)=[O:17])=[CH:11][CH:12]=3)[O:7][CH2:6]2)[CH2:3][CH2:2]1.Cl.[Cl:21][C:22]1[CH:29]=[C:28]([NH:30][NH2:31])[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>>[Cl:21][C:22]1[CH:29]=[C:28]([N:30]2[CH:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]3[CH2:6][O:7][C:8]4[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[CH:11]=[CH:12][C:13]=4[C:14]3=[N:31]2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]참가 물질
실험 절차
The title compound was prepared from methyl 3-(cyclopropylmethylene)-4-oxochroman-7-carboxylate; Preparation 33 and 2-chloro-4-hydrazinylbenzonitrile hydrochloride; Preparation 1 according to Method B and Method C. The crude product was purified by reverse-phase HPLC (65 to 85% acetonitrile/water/0.05% trifluoroacetic acid) to give 2-(3-chloro-4-cyanophenyl)-3-cyclopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid (yellow solid, 14 mg). The title compound was largely present as (±)-(3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-cyclopropyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.18 (br. s., 1H), 7.97 (d, J=8.2 Hz, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.59 (dd, J=8.2, 1.6 Hz, 1H), 7.48 (d, J=1.6 Hz, 1H), 7.43 (d, J=2.0 Hz, 1H), 7.23 (dd, J=8.6, 1.6 Hz, 1H), 4.84 (dd, J=10.5, 5.9 Hz, 1H), 4.46 (dd, J=12.9, 10.5 Hz, 1H), 4.39 (t, J=10.0 Hz, 1H), 3.93 (ddd, J=13.1, 10.2, 5.7 Hz, 1H), 0.74-0.85 (m, 1H), 0.63-0.71 (m, 1H), 0.52-0.61 (m, 1H), 0.37-0.45 (m, 1H), 0.18-0.26 (m, 1H).
후처리
- customPreparation 1 according to Method B and Method C
- customThe crude product was purified by reverse-phase HPLC (65 to 85% acetonitrile/water/0.05% trifluoroacetic acid)
출처 및 근거
- ORD 기록
- ord-74a5ae83bcac48d187f299e27c7b2992
- 출처 데이터셋
- uspto-grants-2010_08
- 특허 번호
- US07781428B2
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