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4-Toluenesulfonyl chloride → 2-{6-[Bis(tert-butoxycarbonyl)amino]-4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethyl 4-methylbenzenesulfonate

HRID 1693266
ノート
印刷プレビュー

反応式

HRID 1693266 の反応式
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[C:19]([O:23][C:24]([N:26]([C:34]1[N:39]=[C:38]2[N:40]([CH2:46][C:47]3[C:52]([CH3:53])=[C:51]([O:54][CH3:55])[C:50]([CH3:56])=[CH:49][N:48]=3)[N:41]=[C:42]([CH2:43][CH2:44][OH:45])[C:37]2=[C:36]([Cl:57])[N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:45][CH2:44][CH2:43][C:42]2[C:37]3[C:38](=[N:39][C:34]([N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:25])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:35][C:36]=3[Cl:57])[N:40]([CH2:46][C:47]3[C:52]([CH3:53])=[C:51]([O:54][CH3:55])[C:50]([CH3:56])=[CH:49][N:48]=3)[N:41]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59311523di-tert-butyl{4-chloro-3-(2-hydroxyethyl)-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate

生成物 1

HCID 593114662-{6-[Bis(tert-butoxycarbonyl)amino]-4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}ethyl 4-methylbenzenesulfonate収率 91%

試薬・触媒・溶媒

2
HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (0.048 mL), p-toluenesulfonyl chloride (43 mg) and 4-dimethylaminopyridine (0.7 mg) were added to a mixture composed of di-tert-butyl{4-chloro-3-(2-hydroxyethyl)-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate of 8) above (64 mg) and dehydrated dichloromethane (1 mL) under cooling in an ice bath. The ice bath was removed and the mixture was stirred for 12 hours. The reaction mixture was diluted with ethyl acetate and sequentially washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (74 mg, 91%) as an amorphous substance.

後処理

  1. temperatureunder cooling in an ice bath
  2. customThe ice bath was removed
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-631433f2ceac4770acc98b76d2e628b3
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158638B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート