1-Hydroxybenzotriazole → [4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone

HRID 80548

Reaktionsgleichung

Reaktionsgleichung von HRID 80548
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.[N:19]1([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[N:19]1([CH:24]2[CH2:29][CH2:28][N:27]([C:13]([C:12]3[CH:11]=[CH:10][C:9]([B:4]4[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]4)=[CH:17][CH:16]=3)=[O:15])[CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 787034-(1-Pyrrolidinyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Produkt 1

HCID 57886103[4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid (9.80 mmol, 2.43 g), 4-(1-pyrrolidinyl)piperidine (10.77 mol, 1.66 g), 1-hydroxybenzotriazole (16.67 mmol, 2.25 g), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (19.57 mmol, 3.75 g) in DMF (30 mL) was stirred overnight at 60° C. Upon removal of DMF on rotavap, the residue was taken into mixture of EtOAc and H2O. The combined organic layers from extraction were stirred with aq. 2N HCl for 20 min and the aqueous layer was purified by reverse phase prep-HPLC to furnish the desired boronic acid (1.24 g. 42%).

Aufarbeitung

  1. customUpon removal of DMF on rotavap
  2. additionthe residue was taken into mixture of EtOAc and H2O
  3. extractionThe combined organic layers from extraction
  4. customthe aqueous layer was purified by reverse phase prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2b9a53560a5e4de0a9233069280129c6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846664B2

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