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Dichloromethane → Benzyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate

HRID 1517333
ノート
印刷プレビュー

反応式

HRID 1517333 の反応式
C(N(C(C)C)CC)(C)C.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].ClCCl.[CH3:24][S:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]1[CH:42]=[C:41]([O:43][CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[N:40]=[CH:39][N:38]=1)[CH2:32][CH2:31]2)(=[O:27])=[O:26]>O>[CH3:24][S:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]1[N:38]=[CH:39][N:40]=[C:41]([O:43][CH:44]3[CH2:49][CH2:48][N:47]([C:11]([O:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[O:12])[CH2:46][CH2:45]3)[CH:42]=1)[CH2:32][CH2:31]2)(=[O:27])=[O:26]
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 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

生成物 1

HCID 68562874Benzyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

Diisopropylethylamine (93 μL, 0.53 mmol) and benzyl chloroformate (57 μL, 0.40 mmol) were added at 0° C. to a dichloromethane (5 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (100 mg, 0.267 mmol) produced in Reference Example 28, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, water was added, followed by extraction with dichloromethane three times. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-1:1, V/V). The obtained crude product was washed with diisopropyl ether to obtain the title compound as white powder (67.3 mg, yield: 50%).

後処理

  1. customproduced in Reference Example 28
  2. extractionfollowed by extraction with dichloromethane three times
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-1:1, V/V)
  7. customThe obtained crude product
  8. washwas washed with diisopropyl ether

出典と根拠

ORDレコード
ord-6521abd331fd4599bdb29d429a647ef8
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08232287B2

反応ノート

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