2-azido-1-(4-methylphenyl)ethanone → [8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester

HRID 1785571

Reaktionsgleichung

Reaktionsgleichung von HRID 1785571
[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]([CH3:50])=[CH:46][CH:45]=1)=[O:43])=[N+]=[N-].N(CC(C1C=CC(C(F)(F)F)=CC=1)=O)=[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]([CH3:50])=[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]

Komponenten

5

Edukt 4

HCID 110084392-azido-1-(4-methylphenyl)ethanoneHCID 53416493HCID 53416493, VerbindungHCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthaleneHCID 86609614HCID 86609614, Verbindung

Produkt 1

HCID 67229286[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl esterAusbeute 83 %

Versuchsvorschrift

The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (188 mg, 0.618 mmol) for the product of Example 1F and the product of Example 9A (130 mg, 0.741 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with 2% to 5% CH3OH/CH2Cl2 followed by 60% EtOAc/hexanes which gave 215 mg (83%) of the title compound as a yellow amorphous solid. 1H NMR (DMSO-d6) δ 9.06 (br s, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.29 (s, 1H), 7.23 (d, J=8.1 Hz, 2H), 7.10 (t, J=7.8 Hz, 1H), 6.98 (br d, 1H), 6.84 (d, J=7.5 Hz, 1H), 3.65 (m, 1H), 3.02 (m, 1H), 2.83 (m, 2H), 2.42 (m, 1H), 2.31 (s, 3H), 1.87 (m, 1H), 1.58 (m, 1H), 1.39 (s, 9H); MS (ESI+) m/z 420 (M+H)+.

Aufarbeitung

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 2% to 5% CH3OH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-61106ec27caa41878b6dc1c4c80983f5
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504520B2

Verknüpfte Notizen

Wird geladen…