Propionamide → N-[4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6-dihydro-isoquinolin-8-yl]-propionamide

HRID 530371

Reaktionsgleichung

Reaktionsgleichung von HRID 530371
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:21]4[CH2:20][CH2:19][CH2:18][C:17](=O)[C:16]=4[CH:15]=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:23].[C:24]([NH2:28])(=[O:27])[CH2:25][CH3:26].FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>FC(F)(F)C1C=CC=CC=1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:21]4[CH2:20][CH2:19][CH:18]=[C:17]([NH:28][C:24](=[O:27])[CH2:25][CH3:26])[C:16]=4[CH:15]=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:23]

Komponenten

6

Edukt 4

HCID 6578Propionamide2×HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acid3×HCID 715387441-methyl-6-(8-oxo-5,6,7,8-tetrahydro-isoquinolin-4-yl)-3,4-dihydro-1H-quinolin-2-one

Produkt 1

HCID 71538745N-[4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6-dihydro-isoquinolin-8-yl]-propionamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7368(Trifluoromethyl)benzeneLösungsmittel3×

Reaktionsbedingungen

Temperatur
102 °C

Versuchsvorschrift

To a stirred suspension of 1-methyl-6-(8-oxo-5,6,7,8-tetrahydro-isoquinolin-4-yl)-3,4-dihydro-1H-quinolin-2-one) (919 mg, 3 mmol, example 70) and propionic acid amide (658 mg, 9 mmol) in trifluorotoluene (30 mL) was added trifluoromethane sulfonic acid (585 mg, 3.9 mmol) and the reaction was stirred at 102° C. After 4 h, a solution of trifluoromethane sulfonic acid (158 mg, 1.05 mmol) in trifluorotoluene (5 mL) was added and the reaction mixture stirred for further 8 h. After this time, propionic acid amide (219 mg, 3 mmol) and a solution of trifluoromethane sulfonic acid (158 mg, 1.05 mmol) in trifluorotoluene (5 mL) were added and the stirring continued at 102° C. over night. The reaction mixture was allowed to cool down to room temperature and aq. NaOH 2 M (30 mL) was added. The resulting mixture was extracted with dichloromethane (3×) and the organic phases washed with aq. sat. NaCl solution (2×). The combined organic phases were dried over Na2SO4, filtered and evaporated. Crystallization of the crude product (dichloromethane/ethyl acetate/heptane) afforded the title compound (915 mg, 84% yield) as off-white crystals. MS: 362.2 (M+H+).

Aufarbeitung

  1. stirringthe reaction mixture stirred for further 8 h
  2. waitthe stirring continued at 102° C. over night
  3. temperatureto cool down to room temperature
  4. extractionThe resulting mixture was extracted with dichloromethane (3×)
  5. washthe organic phases washed with aq. sat. NaCl solution (2×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customCrystallization of the crude product (dichloromethane/ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-56bf8af5568d4410b556036728b2a125
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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