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

반응식

HRID 1812327 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b07f20c8c6184b17ac746789b738b083
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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