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

HRID 337524

反応式

HRID 337524 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7e627cebae7242b3b99a599af6b579b3
出典データセット
uspto-grants-2014_11
特許番号
US08889718B2

関連ノート

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