2-Pyridinemethanamine → 5-methyl-3-phenyl-N-(pyridin-2-ylmethyl)-1,2-oxazole-4-carboxamide

HRID 747857

반응식

HRID 747857 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].C(=O)([O-])O.[Na+].[CH3:14][C:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]=1[C:26](Cl)=[O:27]>O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:26]([C:16]1[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][O:19][C:15]=1[CH3:14])=[O:27]

참가 물질

6

반응물 3

HCID 195092-PyridinemethanamineHCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 7008625-methyl-3-phenyl-N-(pyridin-2-ylmethyl)-1,2-oxazole-4-carboxamide수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매3회

실험 절차

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (4.06 g, 20 mmol, commercially available) and thionyl chloride (5 mL) was heated under reflux for 3 h. Evaporation of all volatiles afforded 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (4.4 g, 93%) as yellow oil, which was used without further purification in the next reaction. To a mixture of an aqueous solution of 2-picolylamine (0.182 g, 1.68 mmol) in water (2 mL) and ethyl acetate (4 mL) were added sodium hydrogen carbonate (362 mg, 4.2 mmol) in one portion. Then, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (0.31 g, 1.4 mmol) in ethyl acetate (2 mL) was added dropwise with vigorous stirring under ice-bath cooling keeping the temperature at 0° C. After addition, the reaction mixture was stirred at room temperature for 18 h. The resulting solution was then diluted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extracts were then washed with brine, dried over sodium sulphate) and concentrated to afford the title compound (0.38 g, 93%) as a white solid. MS: m/e: 294.1 [M+H]+.

후처리

  1. customwas used without further purification in the next reaction
  2. temperaturecooling
  3. customat 0° C
  4. additionAfter addition
  5. stirringthe reaction mixture was stirred at room temperature for 18 h
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined extracts were then washed with brine
  9. dry with materialdried over sodium sulphate) and
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a68f2577e1647dd9cb47a104f332755
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399769B2

연결된 노트

불러오는 중…