Pyrazole → 2-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-6-(1H-Pyrazol-1-Yl)-1,2,3,4-Tetrahydroisoquinoline

HRID 1713102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713102
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH:21]3[CH2:24][CH2:23][CH2:22]3)[CH2:17][CH2:16]1)=[O:14])[CH2:6][CH2:5]2.[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1.C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH:21]1([N:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:7]3[CH2:6][CH2:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([N:25]5[CH:29]=[CH:28][CH:27]=[N:26]5)[CH:3]=4)[CH2:8]3)[CH2:16][CH2:17]2)[CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 574205706-Bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 247515112-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-6-(1H-Pyrazol-1-Yl)-1,2,3,4-Tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 6-bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline (120 mg, 0.307 mmol), pyrazole (31 mg, 0.46 mmol), Cu2O (4 mg, 0.03 mmol), salicylaldoxime (16 mg, 0.12 mmol) and Cs2CO3 (300 mg, 0.92 mmol) in CH3CN (8 mL) is degassed by argon and heated at 120° C. in a sealed tube overnight. EtOAc (10 mL) is added and the mixture is filtered. The organic layer is washed with brine (10 mL) and dried. Purification of the residue by PTLC gives title compound as a light yellow solid. MS (M+1): 380.2; 1H NMR (δ, CDCl3): 7.88 (d, 1H), 7.70 (d, 1H), 7.47 (d, 1H), 7.41 (dd, 1H), 7.08 (d, 1H), 6.45 (dd, 1H), 3.71 (s, 2H), 3.65 (t, 4H), 3.38 (s, 2H), 2.96 (t, 2H), 2.81 (t, 2H), 2.63-2.72 (m, 1H), 2.28 (q, 4H), 1.64-2.08 (m, 6H).

Aufarbeitung

  1. customis degassed by argon
  2. additionEtOAc (10 mL) is added
  3. filtrationthe mixture is filtered
  4. washThe organic layer is washed with brine (10 mL)
  5. customdried
  6. customPurification of the residue by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-3fbd91f6ea6d45cb85018dcf3abc12ce
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795262B2

Notizen zur Reaktion

Wird geladen…