Hydrochloric Acid → Lp-PLA2-IN-1

HRID 920364

Reaktionsgleichung

Reaktionsgleichung von HRID 920364
Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH2:33][OH:34])[CH:18]=[C:19]([F:32])[C:20]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1.[H-].[Na+].Cl>CN(C)C=O>[F:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([F:32])[C:20]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=1)[CH2:33][O:34][C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 66825487(3,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)phenyl)methanol2×HCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Produkt 1

HCID 71236597Lp-PLA2-IN-1Ausbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The title compound was prepared by a procedure similar to that described for E1 starting from 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one and (3,5-difluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol. An exemplary process is shown below: To a solution of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-c]pyrimidin-6(2H)-one, trifluoroacetic acid salt (43 mg, 0.137 mmol) and (3,5-difluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol (46.0 mg, 0.151 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) were added NaH (16.45 mg, 0.411 mmol). The mixture was stirred at room temperature for 30 mins. Sufficient aqueous HCl solution (1 M) was added to adjust the solution to pH to ˜7. The resulted mixture was purified by Mass Directed AutoPrep (basic mobile phase) to afford the title compound (18 mg, 0.038 mmol, 28.0% yield) as a white solid.

Aufarbeitung

  1. customThe title compound was prepared by a procedure similar to
  2. customThe resulted mixture was purified by Mass Directed AutoPrep (basic mobile phase)

Quellen und Nachweise

ORD-Eintrag
ord-5d31e3912ec14110b258e1b5f2f2e1d0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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