Hydrochloric Acid → 4-(4-Aminofuro[3,2-c]pyridin-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1910667노트

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HRID 1910667 반응식
[C:1]([C:3]1[CH:8]([C:9]2[O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:18]C(=O)C4C=CC=CC=4)[C:11]=3[CH:10]=2)[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]=1[CH3:30])#[N:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[NH2:18][C:12]1[C:11]2[CH:10]=[C:9]([CH:8]3[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]([CH3:30])=[C:3]3[C:1]#[N:2])[O:17][C:16]=2[CH:15]=[CH:14][N:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 10340Sodium CarbonateHCID 52938807N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

생성물 1

HCID 529205034-(4-Aminofuro[3,2-c]pyridin-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile수율 18%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A solution of 43 mg (0.11 mmol) N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide (Example 4) in acetic acid (3 ml) was treated with 0.2 ml hydrochloric acid (37%) and stirred for 24 h at 100° C. Then, further 0.2 ml hydrochloric acid (37%) were added, and stirring was continued for 48 h at 100° C. Upon cooling, saturated aq. sodium carbonate solution was added until a neutral pH was reached. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v) to afford the title compound (5.6 mg, 18% of th.) as a white solid.

후처리

  1. stirringstirring
  2. waitwas continued for 48 h at 100° C
  3. temperatureUpon cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine and water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v)

출처 및 근거

ORD 기록
ord-671a3c3159754a598f2e9892b1b64c49
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604028B2

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