Bis(2-chloroethyl) ether → HCID 178422096, 화합물

HRID 46138

반응식

HRID 46138 반응식
[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

참가 물질

6

반응물 4

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178422098HCID 178422098, 화합물

생성물 1

HCID 178422096HCID 178422096, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f71f156c292417a81d4bc3450cb246d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541592B2

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