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 1710862ノート

反応式

HRID 1710862 の反応式
[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

参加物

7

反応物 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

生成物 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-amine収率 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-amine収率 69%

試薬・触媒・溶媒 1

HCID 86628431Dioxomolybdenum(2+) dichloride触媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fdf2cd2e1cf8419aba1ff3bdf3905407
出典データセット
uspto-grants-2010_09
特許番号
US07790737B2

反応ノート

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