Dimethylacetamide → N-cyclohexyl-5-[(5H-imidazo[4,5-c]pyridin-5-yl)methyl]N-methyl-2-furancarboxamide

HRID 981057

반응식

HRID 981057 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[N:3]=[CH:2]1.[CH2:10](Cl)[C:11]1[O:15]C=[CH:13][CH:12]=1.[CH3:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19]>>[CH:21]1([N:20]([CH3:22])[C:18]([C:17]2[O:15][C:11]([CH2:10][N:9]3[CH:8]=[CH:7][C:6]4=[N:3][CH:2]=[N:1][C:5]4=[CH:4]3)=[CH:12][CH:13]=2)=[O:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

4

반응물 3

HCID 31374DimethylacetamideHCID 67504Imidazo(4,5-b)pyridineHCID 2195202-(Chloromethyl)furan

생성물 1

HCID 20071642N-cyclohexyl-5-[(5H-imidazo[4,5-c]pyridin-5-yl)methyl]N-methyl-2-furancarboxamide수율 65%

반응 조건

온도
75 °C

실험 절차

To a stirred solution of imidazopyridine (150 mg, 1.25 mmol) in dimethylacetamide (30 mL) under argon, furfuryl chloride (product of Example H) (320 mg. 1.25 mmol) was added in one portion. The reaction temperature was slowly raised to 75° C. and was stirred for 60 hr. The reaction flask was cooled to room temperature and the solvent was removed under reduced pressure at <45° C. The residue obtained was triturated with excess of dry ether and filtered. The crude product (410 mg) was chromatographed (silica gel, CH2Cl2 :MeOH:NH4OH::90:10:1) to give the title compound (265 mg, 65%) as white solid, mp 189-90° C., 1H NMR (CDCl3) 1H NMR (CDCl3) 0.85 -1.9(m, 13H), 3.6-3.8 & 4.3-4.45(m, 1H), 5.62 (s, 2H), 6.62 (brs, 1H), 6.82 (brs, 1H), 7.73 (dd, J=7 Hz, 1H), 7.85 (dd, J=3,7 Hz, 1H), 8.57 (s, 1H), 8.8 ppm (s, 1H), Anal calcd. for C19H22N4O2 0.5H2O: C, 65.70,H,6.62, N, 16.11. Found: C, 65.65, H, 6.71, N, 16.06.

후처리

  1. temperatureThe reaction flask was cooled to room temperature
  2. customthe solvent was removed under reduced pressure at <45° C
  3. customThe residue obtained
  4. customwas triturated with excess of dry ether
  5. filtrationfiltered
  6. customThe crude product (410 mg) was chromatographed (silica gel, CH2Cl2 :MeOH:NH4OH::90:10:1)

출처 및 근거

ORD 기록
ord-8d777e38b5e84e1ba4e32a92fdea0dc4
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990518

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