Triethylamine → HCID 86670971, Verbindung

HRID 515340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515340
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:32])[CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][C:3]=1[F:33].Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].Cl.[O:48]1[CH2:52][CH2:51][C@H:50]([NH2:53])[CH2:49]1.C(N(CC)CC)C>O1CCCC1>[F:33][C:3]1[CH:4]=[C:5]([CH:8]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:31])([C:27]([F:30])([F:28])[F:29])[C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)[CH2:13][CH2:14]2)[OH:32])[CH:6]=[CH:7][C:2]=1[NH:1][C:35]([NH:53][C@H:50]1[CH2:51][CH2:52][O:48][CH2:49]1)=[O:36]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86670969HCID 86670969, Verbindung

Produkt 1

HCID 86670971HCID 86670971, VerbindungAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-((4-((4-Amino-3-fluorophenyl)(hydroxy)methyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.125 mmol, 60 mg) and 4-nitrophenyl chloroformate (0.125 mmol, 25.2 mg) were combined in tetrahydrofuran (2 mL) and the reaction stirred at room temperature for 1 hour. (S)-Tetrahydrofuran-3-amine hydrochloride (0.125 mmol, 15.43 mg) and triethylamine (0.500 mmol, 50.6 mg) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane) to afford the title compound (13 mg). MS (ESI) m/z 594.7 [M+H]+

Aufarbeitung

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c902277b774a46f7bc7664b995d945f2
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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