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Triethylamine → (4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

HRID 1798547
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1798547
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=O.CN(C(ON1N=N[C:23]2[CH:24]=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N([CH2:42][CH3:43])CC)C.[CH:44]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)([CH3:46])[CH3:45].[CH3:53]COC(C)=O>>[CH:44]([N:47]1[CH2:52][CH2:51][N:50]([C:1]([C:4]2[CH:9]=[CH:8][C:7]([B:10]3[O:12][C:23]([CH3:24])([CH3:22])[C:42]([CH3:43])([CH3:53])[O:11]3)=[CH:6][CH:5]=2)=[O:3])[CH2:49][CH2:48]1)([CH3:46])[CH3:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 780131-IsopropylpiperazineHCID 3121834-Carboxyphenylboronic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 68756040
(4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Versuchsvorschrift

4-Carboxyphenylboronic acid, pinacol ester (1.0 eq, 2.01 mmol, 500 mg) and HATU (2.0 eq, 4.02 mmol, 1.53 g) are mixed together in DMF peptide grade (10 mL). Triethylamine (1.2 eq, 2.41 mmol, 0.34 mL) is then added dropwise and the resulting reaction solution is allowed to stir at room temperature for 15 minutes. Isopropylpiperazine (1.2 eq, 2.41 mmol, 0.35 mL) is then added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo and dried under vacuum at 40° C. to afford the title compound; [M+H]+=359.

Aufarbeitung

  1. customthe resulting reaction solution
  2. stirringthe reaction mixture is stirred at room temperature overnight
  3. washwashed with water
  4. customThe organic layer is dried
  5. dry with materialover drying agent MgSO4
  6. filtrationfiltered
  7. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-8ecc25e677084acdbd058531bd897948
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343966B2

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