4-Nitrophenyl pyridin-2-ylcarbamate → HCID 42635101, Verbindung

HRID 445275

Reaktionsgleichung

Reaktionsgleichung von HRID 445275
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28](=O)[O:29]C1C=CC([N+]([O-])=O)=CC=1>CC#N>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)=[O:29]

Komponenten

4

Edukt 2

HCID 103327734-Nitrophenyl pyridin-2-ylcarbamateHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 42635101HCID 42635101, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.361 mmol) in MeCN (2 mL) was added 4-nitrophenyl pyridin-2-ylcarbamate (467 mg, 1.80 mmol). The resulting mixture was then heated at 70° C. for 16 h, cooled to RT and filtered. The white solid obtained was washed with DCM (2×2 mL). The combined filtrates were then concentrated and the residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane) to give the title compound as a colorless solid. MS (ESI, positive ion) m/z: 398 (M+H).

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. customThe white solid obtained
  4. washwas washed with DCM (2×2 mL)
  5. concentrationThe combined filtrates were then concentrated
  6. customthe residue purified by silica gel flash column chromatography (0%-100% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-59df1fca6aae47fb8e7587a497fdab4b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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