m-Chloroperbenzoic acid → 9-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926124

Reaktionsgleichung

Reaktionsgleichung von HRID 926124
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]4[CH2:20][O:19]4)=[CH:17][C:12]=3[C:11]3=[N:21][CH:22]=[N:23][N:10]3[C:9]2=[O:24])=[CH:5][CH:4]=1.ClC1C=CC=[C:30]([C:34]([O:36]O)=O)C=1.COC1C=C[C:43]([CH2:44][N:45]2C3N=CC(C=C)=CC=3C3=NC=NN3C2=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:19][CH:18]([C:16]1[CH:15]=[N:14][C:13]2[N:8]([CH2:7][C:6]3[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:9](=[O:24])[N:10]3[N:23]=[CH:22][N:21]=[C:11]3[C:12]=2[CH:17]=1)[CH2:20][N:45]1[CH2:30][CH2:34][O:36][CH2:43][CH2:44]1

Komponenten

6

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 867053866-(4-methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneHCID 1181150326-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Produkt 1

HCID 727063249-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one. 3-Chloroperbenzoic acid (139 mg, 0.62 mmol) was added to a stirred solution of 6-(4-methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 30, 138 mg, 0.41 mmol) in DCM (1.3 mL) and the mixture was stirred for 18 h. Saturated sodium bicarbonate (3 mL) was added to the reaction mixture and the mixture was stirred for 2 h. The reaction mixture was diluted with DCM (5 mL), and the organic layer was separated, dried (MgSO4), and concentrated under vacuum to afford the title compound (118 mg, 82%) as a yellow semi-solid, which was used without further purification in the next step.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 h
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-42d1fde8c5de4b68acb5a1cece9d55a0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284335B2

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