Butyric Acid → 7-methyl-2-propyl-6-[(1-oxobutyl)amino]3H-imidazo[4,5-b]pyridine

HRID 36114

반응식

HRID 36114 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1.[CH2:15]1[CH2:19][O:18][CH2:17][CH2:16]1.[C:20](O)(=O)[CH2:21][CH2:22][CH3:23].[NH4+].[OH-]>O.[Ni].CO>[O:18]=[C:17]([NH:12][C:5]1[C:6]([CH3:11])=[C:7]2[NH:8][C:20]([CH2:21][CH2:22][CH3:23])=[N:1][C:2]2=[N:3][CH:4]=1)[CH2:16][CH2:15][CH3:19]

참가 물질

8

반응물 4

HCID 264Butyric AcidHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 50863994-Methyl-3,5-dinitropyridin-2-amine

생성물 1

HCID 199397377-methyl-2-propyl-6-[(1-oxobutyl)amino]3H-imidazo[4,5-b]pyridine

시약·촉매·용매 3

HCID 935Nickel촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

A mixture of 2-amino-3,5-dinitro-4-methylpyridine (3.1 g, 15.6 mmol), THF (100 mL), methanol (100 mL) and Raney-nickel (6 mL of a 1:1 suspension in H2O) was stirred under H2 (1 atm.) for 6 h. The mixture was quickly filtered into a receiving flask containing 3 mL of conc. aqueous HCl, and the solvent was removed in vacuo at r.t. To the resulting crude 2,3,5-triamino-3-methylpyridine.HCl complex was added butyric acid (4.3 mL, 46.9 mmol) and polyphosphoric acid (100 mL) and this mixture was heated to 85° C. for 10 h. The warmed mixture was poured into stirred ice-H2O (200 mL) and this mixture was cooled and neutralized (to pH 3) by the addition of conc. NH4OH. Extraction with CH2Cl2 (3×50 mL), drying (Na2SO4), and concentration gave the title compound as a solid.

후처리

  1. filtrationThe mixture was quickly filtered into a receiving flask
  2. additioncontaining 3 mL of conc. aqueous HCl
  3. customthe solvent was removed in vacuo at r.t
  4. additionThe warmed mixture was poured
  5. temperaturethis mixture was cooled
  6. extractionExtraction with CH2Cl2 (3×50 mL)
  7. customdrying
  8. concentration(Na2SO4), and concentration

출처 및 근거

ORD 기록
ord-fc41fdc5d05c49e9b0278ac7ee56e708
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412097

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