Hydrochloric Acid → 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochloride

HRID 882281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882281
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:32]=[CH:31][C:17]([C:18]([NH:20][CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:42])(=[O:3])[CH3:2].[ClH:43]>O1CCOCC1>[ClH:43].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:32]=[CH:31][C:17]([C:18]([NH:20][CH2:21][CH2:22][NH2:23])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:42])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86709419tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate

Produkt 1

HCID 714685074-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochlorideAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A suspension of tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate (for a preparation see Intermediate 39)(65 mg, 0.114 mmol) in 1,4-dioxane (1 mL) at room temperature was treated with hydrogen chloride in 1,4-dioxane (4N, 2 mL, 8.00 mmol) and the resulting suspension was stirred at this temperature for 1 h then concentrated in vacuo. The precipitate formed was triturated with Et2O isolated by filtration and dried under vacuum to give 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochloride (60 mg, 0.119 mmol, 104% yield) as a white solid. LCMS (HpH, 2 min), Rt=0.75 min, MH+=469.

Aufarbeitung

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. customThe precipitate formed
  4. customwas triturated with Et2O
  5. customisolated by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-19ea80fed62a40829159e3ab2c8b51f5
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993554B2

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