Pyridine → N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide

HRID 714350

반응식

HRID 714350 반응식
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=1)[C:13]([OH:15])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.O[N:26]=[C:27]([NH2:35])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>ClCCl.CN(C)C=O.C(OCC)(=O)C>[CH2:28]([C:27]1[N:35]=[C:13]([C:12]2[CH:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=2)[O:15][N:26]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

9

반응물 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 2731007N'-hydroxy-2-phenylethanimidamideHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 64393851HCID 64393851, 화합물

생성물 1

HCID 67153834N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-benzamidoisonicotinic acid (0.35 g, 1.44 mmol) and N,N-dimethylformamide (0.1 mL) in dichloromethane (5 mL) was added oxalyl chloride (0.15 mL, 1.73 mmol) at ambient temperature. The resulting mixture was stirred at ambient temperature for 1 hour and concentrated in vacuo to dryness. The residue was dissolved in N,N-dimethylformamide (2 mL) and added to a solution of N′-hydroxy-2-phenylacetimidamide (0.24 g, 1.59 mmol) and pyridine (0.3 mL, 3.70 mmol) in N,N-dimethylformamide (1 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours, diluted with ethyl acetate (40 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was dissolved in toluene (10 mL), followed by the addition of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (0.53 g, 2.16 mmol). The mixture was refluxed for 1 hour and concentrated in vacuo. The residue was purified by column chromatography to give N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide as a colorless solid (0.06 g 12%): mp 150-151° C.; 1H NMR (300 MHz, CDCl3) δ 9.06 (s, 1H), 8.69 (s, 1H), 8.46 (d, J=4.9 Hz, 1H), 7.94-7.91 (m, 2H), 7.72-7.69 (m, 1H), 7.62-7.48 (m, 3H), 7.39-7.24 (m, 5H), 4.16 (s, 2H); MS (ES+) m/z 357.5 (M+1).

후처리

  1. concentrationconcentrated in vacuo to dryness
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (2 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 3 hours
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in toluene (10 mL)
  9. temperatureThe mixture was refluxed for 1 hour
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a056803727484e82aaaf77c0a5bf2208
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187426B2

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