Acetic Acid → 2-Chloro-6-methyl-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyridine

HRID 2059663노트

반응식

HRID 2059663 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([NH:7][OH:8])=[NH:6].[C:13](O)(=O)[CH3:14]>CC(C)(C)C([O-])([O-])[O-]>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:13]([CH3:14])[O:8][N:7]=2)[CH:9]=[C:10]([CH3:12])[N:11]=1

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 178426669HCID 178426669, 화합물

생성물 1

HCID 595344432-Chloro-6-methyl-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyridine

시약·촉매·용매 1

HCID 21927715Trimethylorthoacetate용매

반응 조건

온도
100 °C

실험 절차

2-Chloro-N-hydroxy-6-methyl-isonicotinamidine (120 mg) was suspended in trimethylorthoacetate (3 ml) under inert atmosphere and acetic acid (0.3 ml) was added. The mixture was heated to 100° C. and stirred for 2 h. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue partitioned between EtOAc and aqueous solution of NaHCO3. The organic layer was separated, washed with water and brine, dried under Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 9/1) affording the title compound (107 mg).

후처리

  1. additionwas added
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas evaporated under reduced pressure
  4. customthe residue partitioned between EtOAc and aqueous solution of NaHCO3
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. customdried under Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customThe crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 9/1)

출처 및 근거

ORD 기록
ord-a3f386dfd32f4497a39099a5a1eed0ca
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278302B2

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