Triethylamine → 2-Amino-4-(2-pyridyl)thiazol-5-yl 2-pyridyl ketone

HRID 337524

반응식

HRID 337524 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10].BrBr.C(N(CC)CC)C.[NH2:27][C:28]([NH2:30])=[S:29].C(=O)([O-])O.[Na+]>C(O)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]([C:8]1[S:29][C:28]([NH2:30])=[N:27][C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:10]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 27284941,3-Di(2-pyridyl)-1,3-propanedione

생성물 1

HCID 231446682-Amino-4-(2-pyridyl)thiazol-5-yl 2-pyridyl ketone수율 51%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

1,3-Di(2-pyridyl)propane-1,3-dione (1.17 g, 5.15 mmol) was dissolved in acetic acid (20 mL), and bromine (856 mg, 5.35 mmol) was added thereto, followed by stirring at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was suspended in ethanol (30 mL), and triethylamine (0.750 mL, 5.38 mmol) and thiourea (416 mg, 5.47 mmol) were added thereto, followed by stirring under heating and reflux for 30 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1) to afford the entitled Compound 630 (739 mg, 51%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringby stirring
  3. temperatureunder heating
  4. temperaturereflux for 30 minutes
  5. extractionfollowed by extraction with chloroform
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1)

출처 및 근거

ORD 기록
ord-7e627cebae7242b3b99a599af6b579b3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889718B2

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