Bis(2-chloroethyl) ether → HCID 178422096、化合物

HRID 46138

反応式

HRID 46138 の反応式
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][CH:34]=1)[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]2([CH3:31])[S:21][C:20]([NH:22][C@H:23]3[CH2:28][CH:27]4[CH2:29][CH:24]3[CH2:25][CH2:26]4)=[N:19][C:18]2=[O:30])[CH2:12][CH2:11]1)=[O:9].C([O-])([O-])=O.[K+].[K+].Cl[CH2:42][CH2:43][O:44][CH2:45][CH2:46]Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:24]12[CH2:29][CH:27]([CH2:26][CH2:25]1)[CH2:28][C@@H:23]2[NH:22][C:20]1[S:21][C:17]([CH3:31])([CH2:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8](=[O:9])[C:7]3[CH:32]=[CH:33][CH:34]=[C:5]([O:4][CH2:3][CH2:2][N:1]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[CH:6]=3)[CH2:11][CH2:12]2)[C:18](=[O:30])[N:19]=1

参加物

6

反応物 4

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178422098HCID 178422098、化合物

生成物 1

HCID 178422096HCID 178422096、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-((1-(3-(2-aminoethoxy)benzoyl)piperidin-4-yl)methyl)-2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methylthiazol-4(5H)-one (100 mg, 0.207 mmol), K2CO3 (114 mg, 0.83 mmol), KI (Aldrich, 6.9 mg, 0.041 mmol), 1-chloro-2-(2-chloroethoxy)ethane (Aldrich, 38 mg, 0.27 mmol) in CH2Cl2 (3 mL) was heated at reflux for 10 d. Saturated NaHCO3 (50 mL) was added, and the crude product was extracted with CH2Cl2 (4×60 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography (silica gel, CH2Cl2 with 0-4% MeOH) afforded the title compound as a colorless thin film (10 mg). MS (ESI, pos. ion) m/z: 555 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 10 d
  3. extractionthe crude product was extracted with CH2Cl2 (4×60 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8f71f156c292417a81d4bc3450cb246d
出典データセット
uspto-grants-2013_09
特許番号
US08541592B2

関連ノート

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