Potassium Bicarbonate → HCID 178491890, 화합물

HRID 1498167노트

반응식

HRID 1498167 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 178491890HCID 178491890, 화합물수율 54%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

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 (1 H, s), 7.89 (1 H, s), 7.83 (1 H, s), 7.26 (1 H, s) 6.88 (1 H, s), 4.01 (3 H, s), 1.58 (6 H, d, J=6.63 Hz).

후처리

  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

출처 및 근거

ORD 기록
ord-1a44c186694e4664b390569c4e114d03
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198918B2

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