Hydrogen Peroxide → N-{1-[3,5-bis(trifiuoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-amine

HRID 906326노트

반응식

HRID 906326 반응식
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([CH:13]([N:15]([CH2:27][C:28]2[C:33]([N:34]([CH2:37][CH:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:35][CH3:36])=[CH:32][CH:31]=[C:30]([O:43][CH3:44])[N:29]=2)[C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][S:25][CH3:26])=[CH:18][N:17]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.OO.[S:49]([O-:52])([O-])=[O:50].[Na+].[Na+].[C:55](#N)C>[Cl-].[Cl-].[Mo+2](=O)=O>[F:46][C:2]([F:1])([F:45])[C:3]1[CH:4]=[C:5]([CH:13]([N:15]([CH2:27][C:28]2[C:33]([N:34]([CH2:37][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42]3)[CH2:35][CH3:36])=[CH:32][CH:31]=[C:30]([O:43][CH3:44])[N:29]=2)[C:16]2[N:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][S:25]([CH3:26])=[O:50])=[CH:20][N:21]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1.[F:46][C:2]([F:1])([F:45])[C:3]1[CH:4]=[C:5]([CH:13]([N:15]([CH2:27][C:28]2[C:33]([N:34]([CH2:37][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42]3)[CH2:35][CH3:36])=[CH:32][CH:31]=[C:30]([O:43][CH3:44])[N:29]=2)[C:16]2[N:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][S:49]([CH3:55])(=[O:52])=[O:50])=[CH:20][N:21]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 24437Sodium SulfiteHCID 25012937N-{1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine

생성물 2

HCID 25012936N-{1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylsulfinyl)ethoxy]pyrimidin-2-amine수율 10%HCID 25013093N-{1-[3,5-bis(trifiuoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-amine수율 69%

시약·촉매·용매 1

HCID 86628431Dioxomolybdenum(2+) dichloride촉매

실험 절차

A solution of N-{1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine (82 mg, 0.12 mmol) obtained in Example 1 in acetonitrile (3 mL) was added with molybdenum dioxide dichloride (3.6 mg, 0.018 mmol) and 30% aqueous hydrogen peroxide (55 mg, 0.49 mmol), and the mixture was stirred at room temperature for 23 hours. The reaction mixture was added with saturated aqueous sodium sulfite, and the mixture was extracted with chloroform. Then, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by preparative silica gel thin layer chromatography (hexane:acetone=3:2) to obtain N-{1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylsulfinyl)ethoxy]pyrimidin-2-amine (compound of Example 2, 8.4 mg, 10%) as yellow oil, and N-{1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-amine (compound of Example 3, 59.5 mg, 69%) as pale yellow oil.

후처리

  1. extractionthe mixture was extracted with chloroform
  2. washThen, the organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by preparative silica gel thin layer chromatography (hexane:acetone=3:2)

출처 및 근거

ORD 기록
ord-ae816b11276141d2a9447333f2f5e044
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012989B2

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