2-Azido-1-[4-(trifluoromethyl)phenyl]ethanone → {8-[5-(4-Trifluoromethylphenyl)oxazol-2-ylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester

반응식

[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([N:18]=[C:19]=S)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC1CC2C(CC=1)=CC=CC=2N=C=S)C.[N:38]([CH2:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=1)=[O:43])=[N+]=[N-]>>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([NH:18][C:19]3[O:43][C:42]([C:44]4[CH:49]=[CH:48][C:47]([C:50]([F:51])([F:52])[F:53])=[CH:46][CH:45]=4)=[CH:41][N:38]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

반응물 3

HCID 534164932-Azido-1-[4-(trifluoromethyl)phenyl]ethanone

HCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

HCID 86609614(8-Isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)carbamic acid tert-butyl ester

생성물 1

HCID 67229897{8-[5-(4-Trifluoromethylphenyl)oxazol-2-ylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester수율 37%

실험 절차

The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (215 mg, 0.706 mmol) for the product of Example 1F, and the product of Example 1G (194 mg, 0.848 mmol). The crude product was purified by flash chromatography eluting with 20% EtOAc/hexane which gave 123 mg (37%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.32 (br s, 1H), 7.75 (m, 4H), 7.60 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.12 (t, J=7.8 Hz, 1H), 6.98 (br d, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.64 (m, 1H), 3.02 (m, 1H), 2.84 (m, 2H), 2.42 (m, 1H), 1.87 (m, 1H), 1.60 (m, 1H), 1.39 (s, 9H); MS (ESI+) m/z 474 (M+H)+.