Triethylamine → tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylate

HRID 515295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515295
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:22].Cl[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[CH3:36][C:37]([NH2:41])([CH3:40])[CH2:38][NH2:39].C(N(CC)CC)C>O1CCCC1>[NH2:41][C:37]([CH3:40])([CH3:36])[CH2:38][NH:39][C:24](=[O:25])[NH:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:11][CH2:12]2)=[CH:4][C:3]=1[F:22]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 821294-Nitrophenyl chloroformateHCID 67193052Tert-butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate

Produkt 1

HCID 86670947tert-Butyl 4-(4-(3-(2-amino-2-methylpropyl)ureido)-3-fluorobenzyl)piperidine-1-carboxylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(4-amino-3-fluorobenzyl)piperidine-1-carboxylate (3.44 mmol, 1.06 g) and 4-nitrophenyl chloroformate (3.44 mmol, 0.693 g) were combined in tetrahydrofuran (5 mL) and the reaction stirred at room temperature for 1 hour. 2-Methylpropane-1,2-diamine (3.44 mmol, 0.303 g) and triethylamine (10.31 mmol, 1.043 g) 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 20% methanol/dichloromethane) to afford the title compound (960 mg). MS (ESI) m/z 423.2 [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 20% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-46e7ad5f7586464a8fef1c688ae03645
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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