Dimethylamine → 5-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid

HRID 1478240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478240
[B:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7](O)=[O:8])([OH:3])[OH:2].[CH3:15][NH:16][CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH3:15][N:16]([CH3:17])[C:7]([C:6]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:4]([B:1]([OH:3])[OH:2])[CH:5]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 426145415-Carboxy-2-methoxybenzeneboronic acid

Produkt 1

HCID 575560785-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acidAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 700 mg (3.57 mmol) 3-borono-4-methoxybenzoic acid in 23 ml DMF, 3.6 ml (7.14 mmol) dimethylamine, 1.5 g (3.93 mmol) HATU and 1.57 ml (14.29 mmol) NMM were added and stirred at RT for 2 hours. The reaction mixture was extracted with EtOAc and water. The organic phase was dried over Na2SO4, filtered and evaporated. The residue was purified by preparative HPLC (Prep. HPLC method 1, gradient: 15-30% in 16 minutes). The fractions containing product were combined and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated to afford 361 mg (1.619 mmol, 45.3% yield) of the title compound as a colorless solid. LCMS: (M+H)=224; tR=0.54 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) δ ppm 7.56 (m, 1H) 7.44 (dd, 1H) 6.99 (d, 1H) 3.81 (s, 3H) 2.93 (s, 6H).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with EtOAc and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative HPLC (Prep. HPLC method 1, gradient: 15-30% in 16 minutes)
  6. additionThe fractions containing product
  7. extractionextracted twice with EtOAc
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4c438aa47c594e108e8b5422e3718a58
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403827B2

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