Trifluoroacetic acid → HCID 44194616, Verbindung

HRID 221514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221514
C(OC(=O)[NH:7][C@H:8]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18]([C:28]([F:31])([F:30])[F:29])=[N:19][C:20]([C:21](=[O:27])[NH:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:14]2[CH2:13]1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:23]([NH:22][C:21]([C:20]1[N:19]=[C:18]([C:28]([F:29])([F:30])[F:31])[N:15]2[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C@H:8]([NH2:7])[CH2:32][C:33]3[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=3[F:41])[CH2:13][C:14]=12)=[O:27])[CH2:24][CH2:25][CH3:26]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57518486HCID 57518486, Verbindung

Produkt 1

HCID 44194616HCID 44194616, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-[3-(1-Butylcarbamoyl-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 43a (120 mg, 0.198 mmol) was dissolved in 10 mL of dichloromethane, and trifluoroacetic acid (452 mg, 3.97 mmol) was then added to the solution. The reaction mixture was stirred at room temperature for 2 hours 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)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid butylamide 43 (70 mg, yield 70%) as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-26828f4cbcc74ad58cf0dfe6d9a173fd
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207161B2

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