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

HRID 2059663ノート

反応式

HRID 2059663 の反応式
[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

参加物

4

反応物 2

HCID 176Acetic AcidHCID 178426669HCID 178426669、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 21927715Trimethylorthoacetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a3f386dfd32f4497a39099a5a1eed0ca
出典データセット
uspto-grants-2012_10
特許番号
US08278302B2

反応ノート

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