Methyl morpholine oxide → 1-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanone

HRID 1812327

Reaktionsgleichung

Reaktionsgleichung von HRID 1812327
[CH3:1][O:2][C:3]1[CH:47]=[CH:46][C:6]([CH2:7][N:8]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:31]([OH:36])[C:32]([F:35])([F:34])[F:33])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([C:31](=[O:36])[C:32]([F:34])([F:33])[F:35])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[N:10]=2)=[CH:46][CH:47]=1

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 666115681-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanol

Produkt 1

HCID 666120731-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanol (preparation described previously in Example 269) (104 mg, 0.161 mmol) and 4 Å molecular sieves in dichloromethane (3.00 mL) was added TPAP (Sigma Aldrich, Inc., 5.64 mg, 0.016 mmol), NMO (Sigma Aldrich, Inc.), 24.45 mg, 0.209 mmol) at room temperature and the mixture was stirred at the same temperature for 1 h and then concentrated. The dark residue was rediluted with ethyl acetate and filtered through a short path of Celite® (diatomaceous earth)/SiO2. The filtered solid was washed with ethyl acetate (3×10 mL). The combined organic phases were concentrated to give a yellow crude residue 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanone which was used directly for the next step without further purification.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe dark residue was rediluted with ethyl acetate
  3. filtrationfiltered through a short path of Celite® (diatomaceous earth)/SiO2
  4. washThe filtered solid was washed with ethyl acetate (3×10 mL)
  5. concentrationThe combined organic phases were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-b07f20c8c6184b17ac746789b738b083
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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