Bromine → N-[4-[4-(4-Methoxyphenyl)-2-methyl-1,3-thiazol-5-YL]-2-pyridyl]benzamide

HRID 1178596노트

반응식

HRID 1178596 반응식
BrBr.[C:3]([NH:11][C:12]1[CH:17]=[C:16]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=O)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:29]([NH2:32])(=[S:31])[CH3:30].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:32]=[C:29]([CH3:30])[S:31][C:18]=2[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:17]=2)=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 219642602-(2-Benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone

생성물 1

HCID 10135691N-[4-[4-(4-Methoxyphenyl)-2-methyl-1,3-thiazol-5-YL]-2-pyridyl]benzamide수율 50%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Bromine (0.18 mL, 3.5 mmol) was added to a solution of 2-(2-benzoylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (1.2 g, 3.4 mmol) in acetic acid (10 mL) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated. The residue was dissolved in N,N-dimethylformamide (20 mL), thioacetamide (0.30 g, 19 mmol) was added to the solution and the mixture was stirred at room temperature for 20 hours. An aqueous saturated solution of sodium hydrogencarbonate (20 mL) was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate and the extract was washed with water. The extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1) to obtain 0.68 g (yield 50%) of the title compound.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (20 mL)
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. customThe extract was dried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1)

출처 및 근거

ORD 기록
ord-b921043187c54ad998da3e04b83e8138
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276527B2

반응 노트

불러오는 중…