Diisopropylethylamine → ethyl 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

HRID 882265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882265
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:25])[CH2:6][C@@H:5]1[CH3:26])(=[O:3])[CH3:2].Cl[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][N:29]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O.CCOC(C)=O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][N:29]=2)[CH2:6][C@@H:5]1[CH3:26])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 67205707ethyl 4-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Produkt 1

HCID 70976688ethyl 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Ethyl 4-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation, see Intermediate 16) (300 mg, 0.851 mmol) and 6-chloronicotinonitrile (236 mg, 1.702 mmol) in anhydrous NMP (5 mL) were treated with DIPEA (0.445 mL, 2.55 mmol). The reaction vial was sealed and heated under microwave irradiation to 200° C. for 2 h. The cooled solution was diluted with water to −20 mL, stirred and the resulting sticky solid isolated by decantation. The solid was dissolved in EtOAc, the solution washed with brine and dried by passing through a hydrophobic frit. The solution was concentrated in vacuo and the residue purified by MDAP (Formate) to give crude ethyl 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (120 mg) as a beige gum which was used directly in the next step without further purification. LCMS: (Formate, 2 min), Rt=1.12 min, MH+455.

Aufarbeitung

  1. customThe reaction
  2. customvial was sealed
  3. customthe resulting sticky solid isolated by decantation
  4. washthe solution washed with brine
  5. customdried
  6. concentrationThe solution was concentrated in vacuo
  7. customthe residue purified by MDAP (Formate)

Quellen und Nachweise

ORD-Eintrag
ord-13bbddb9e35c407eadb4b2697782cb47
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993554B2

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