Ethyl Acetate → Methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate

HRID 562915

反応式

HRID 562915 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1F)#[N:2].C(O[CH2:24][CH3:25])(=O)C>CS(C)=O>[N:2]1([C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=3)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=2[C:1]#[N:2])[CH2:25][CH2:24][CH2:7][CH2:8][CH2:3][CH2:1]1

参加物

4

反応物 2

HCID 8857Ethyl AcetateHCID 66995083Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

生成物 1

HCID 66995069Methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

In 7 ml of DMSO was dissolved 2.22 g of methyl 2-(3-cyano-4-fluorophenyl)isonicotinate, and 2.44 ml of hexamethyleneimine was added thereto, followed by heating at 50° C. for 5 hours. After cooling, the reaction solution was diluted with ethyl acetate and was washed with 1M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and brine, successively. The organic layer was dried and then concentrated under reduced pressure and the resulting residue was dissolved in a mixed solvent of ethyl acetate and diisopropyl ether. Activated carbon was added thereto, followed by stirring for 1 hour. Then, the activated carbon was removed by filtration and washed with ethyl acetate. The resulting filtrate and washing liquid were combined and concentrated to obtain 2.58 g of methyl 2-(4-azepan-1-yl-3-cyanophenyl)isonicotinate. (2) Then, 2.49 g of the compound was dissolved in a mixed solvent of 15 ml of methanol and 30 ml of THF, and 11 ml of a 1M aqueous sodium hydroxide solution was added thereto, followed by heating at 80° C. for 1 hour.

後処理

  1. additionwas added
  2. temperatureAfter cooling
  3. washwas washed with 1M hydrochloric acid
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionthe resulting residue was dissolved in a mixed solvent of ethyl acetate and diisopropyl ether
  7. additionActivated carbon was added
  8. customThen, the activated carbon was removed by filtration
  9. washwashed with ethyl acetate
  10. washThe resulting filtrate and washing liquid
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-639eace32c3a47839a011c2662d7fe62
出典データセット
uspto-grants-2011_11
特許番号
US08067446B2

関連ノート

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