Potassium Bicarbonate → HCID 178491890、化合物

HRID 1530471ノート

反応式

HRID 1530471 の反応式
Cl.[Cl:2][C:3]1[C:8]([C:9]([NH2:11])=[NH:10])=[CH:7][N:6]=[C:5]([O:12][CH3:13])[CH:4]=1.C(=O)(O)[O-].[K+].Cl[CH2:20][C:21]([C:23]1[N:24]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:26][N:27]=1)=O>C1COCC1.O>[Cl:2][C:3]1[C:8]([C:9]2[NH:11][CH:20]=[C:21]([C:23]3[N:24]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:26][N:27]=3)[N:10]=2)=[CH:7][N:6]=[C:5]([O:12][CH3:13])[CH:4]=1

参加物

6

反応物 3

HCID 516893Potassium BicarbonateHCID 670506614-Chloro-6-methoxynicotinimidamide hydrochlorideHCID 712991852-chloro-1-(1-isopropyl-1H-1,2,4-triazol-5-yl)ethanone

生成物 1

HCID 178491890HCID 178491890、化合物収率 54%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 4-chloro-6-methoxy-nicotinamidine hydrochloride (50.9 mmol) and potassium bicarbonate (20.4 g, 202.5 mmol) in THF (128 mL) and water (21 mL) was heated to reflux and treated with a solution of 2-chloro-1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone (9.55 g, 50.9 mmol) in THF (25 mL) added dropwise. The reaction mixture was heated at reflux for 24 h before removal of volatile solvent in vacuo. The resultant residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), treated with charcoal (15 g), filtered and concentrated in vacuo to give a solid. The solid was triturated with 10% diethyl ether in pentane then dried at 50° C. in vacuo to give 4-Chloro-5-[4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-1H-imidazol-2-yl]-2-methoxy-pyridine as a pale brown solid (8.74 g, 54%). LCMS RT=2.86 min, [M+H]+ =319/321. 1H NMR 400 MHz (CDCl3) δ: 9.03 (1H, s), 7.89 (1H, s), 7.83 (1H, s), 7.26 (1H, s) 6.88 (1H, s), 4.01 (3H, s), 1.58 (6H, d, J=6.63 Hz).

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. additionadded dropwise
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 24 h before removal of volatile solvent in vacuo
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. additiontreated with charcoal (15 g)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give a solid
  12. customThe solid was triturated with 10% diethyl ether in pentane
  13. customthen dried at 50° C. in vacuo

出典と根拠

ORDレコード
ord-3d31803ad0ad4653b73299bb3c26f3ea
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

読み込み中…