Pyridine → 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

HRID 1741417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741417
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][NH:19][CH:20]3[C:28]4[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[C:37]([N:19]([CH:20]1[C:28]2[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH2:18][C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)(=[O:39])[CH3:38]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 183673131-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene

Produkt 1

HCID 183674301-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene (0.22 g) and pyridine (0.2 ml) in dichloromethane (5 ml) was added acetyl chloride (0.15 ml) at 0° C. The mixture was stirred for 1.5 hours at the same temperature and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.08 g). MS (m/z): 439 (M+ +1) IR (Nujol): 1640 cm-1NMR (CDCl3, δ): 7.65-7.45 (4H, m), 7.40-7.20 (6H, m), 7.19-7.02 (1H, m), 6.82-6.60 (2H, m), 6.40 (0.5H, t, J=7.5 Hz), 5.56 (0.5H, t, J=7.5 Hz), 4.72 (0.5H, d, J=8.1 Hz), 4.42 (1H, m), 4.19 (0.5H, d, J=8.1 Hz), 3.81 (1.5H, s), 3.78 (1.5H, s), 2.37 (1.5H, s), 3.15-2.92 (1H, n), 2.90-2.64 (1H, m), 2.62-2.42 (1H, m), 2.40-2.10 (1H, m), 2.37 (1.5H, s), 2.35 (1.5H, s)

Aufarbeitung

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic layer was washed with water, sat. NaHCO3, and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2ce20b59777b4add8000bdd2fe18b856
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972965

Notizen zur Reaktion

Wird geladen…