2-Chloropyridine → cis(+/-)-4-Chloro-N-(3-ethoxy-1-pyridin-2-ylpiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide

HRID 43718노트

반응식

HRID 43718 반응식
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

참가 물질

6

반응물 3

HCID 79772-ChloropyridineHCID 10340Sodium CarbonateHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

생성물 1

HCID 86648667cis(+/-)-4-Chloro-N-(3-ethoxy-1-pyridin-2-ylpiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide수율 3.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol), 2-chloropyridine (0.035 mL, 0.37 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMF (1 mL), and the suspension was heated using a microwave reactor at 180° C. for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0) to obtain 3.9 mg of the title compound as a white amorphous solid (3%).

후처리

  1. temperaturethe suspension was heated
  2. customat 180° C.
  3. customfor 30 minutes
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentration under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=7/3→1/0)

출처 및 근거

ORD 기록
ord-3e4d5f62bcc44bf2a0349bb740c8890d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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