Hydrochloric Acid → (R)-1-(1-acetyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-amino-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochloride

HRID 1895644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895644
C(OC(=O)[NH:7][C@H:8]([CH2:28][C:29]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=1[F:37])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:24]([F:27])([F:26])[F:25])=[N:19][C:20]([C:21](=[O:23])[CH3:22])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.[ClH:39]>C(OCC)(=O)C>[ClH:39].[C:21]([C:20]1[N:19]=[C:18]([C:24]([F:27])([F:26])[F:25])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:28][C:29]3[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=3[F:37])[CH2:13][C:14]=12)(=[O:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57518457(R)-[3-(1-acetyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 44194328(R)-1-(1-acetyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-amino-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochlorideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

(R)-[3-(1-Acetyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 27h (0.3 g, 0.55 mmol) was dissolved in 2 mL of ethyl acetate under stirring. A solution of 2.4 N hydrochloric acid in 5 mL of ethyl acetate was then added to the above solution. The reaction mixture was reacted at room temperature and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-1-(1-acetyl-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-3-amino-4-(2,4,5-trifluoro-phenyl)-butan-1-one hydrochloride 27 (0.15 g, yield 57%) as a white solid.

Aufarbeitung

  1. customThe reaction mixture was reacted at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b13ca9c1aed44cf0b9f36b6410ae4aa2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513411B2

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