Acetic Acid → HCID 44232443, Verbindung

HRID 1921232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921232
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][NH:23][CH2:22][CH2:21]2.C(O)(=O)C.ClC(Cl)C.C([BH3-])#N>>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][N:23]([CH2:1][C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[O:13])[N:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH2:22][CH2:21]2

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 498716Cyano-borohydrideHCID 117895946-Chloro-1,2,3,4-tetrahydroisoquinolineHCID 772314531-formyl-4-oxo-4H-quinolizine-3-carboxylic acid

Produkt 1

HCID 44232443HCID 44232443, Verbindung

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 2-5 mL Emrys™ process vial, a mixture of the 1-formyl-4-oxo-4H-quinolizine-3-carboxylic acid (76 mg, 0.35 mmol), 6-chloro-1,2,3,4-tetrahydroisoquinoline (82 mg, 0.49 mmol), glacial acetic acid (0.12 mL, 2.1 mmol) and 1.8 mL of dichloroethane was stirred vigorously. To the stirring mixture was added resin-bound MP-cyanoborohydride (343 mg, 0.70 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 30 minutes. Filtration and solvent removal provided material, which was subjected to preparative reverse phase HPLC. Collection of product containing fractions and removal of solvent yielded the title compound that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 369.1011 calculated for M+H+ [C20H17Cl1N2O3: 369.1001]: 1H NMR (500 MHz, CD3OD) δ 9.59 (d, J=7.1 Hz, 1H), 8.74 (s, 1H), 8.40 (d, J=8.8 Hz, 1H), 8.18 (t, J=73 Hz, 1H), 7.73 (t, J=6.6 Hz, 1H), 7.32 (s, 1H), 7.27 (d, J=8.3 Hz, 1H), 7.14 (d, J=8.6 Hz, 1H), 4.87 (s, 2H), 4.47 (s, 2H), 3.69 (bs, 2H), 3.20 (t, J=6.0 Hz, 2H).

Aufarbeitung

  1. filtrationFiltration and solvent removal
  2. customprovided material, which
  3. customCollection of product
  4. additioncontaining
  5. customfractions and removal of solvent

Quellen und Nachweise

ORD-Eintrag
ord-c7b8c59fb17d4ea9982150af3e656cd9
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173672B2

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