Dimethylformamide → 2,6,7-trimethyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine

HRID 1245901노트

반응식

HRID 1245901 반응식
C[N:2](C)C=O.Cl[C:7]1[C:12]([N+:13]([O-])=O)=[C:11](Cl)[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH2:31])[CH:20]=1.[CH2:32](N(CC)CC)[CH3:33]>>[CH3:32][C:33]1[N:31]([CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[C:11]2[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=[C:7]([NH2:2])[C:12]=2[N:13]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineHCID 219130212-(3-Pyridin-3-ylpropoxy)ethanamine

생성물 1

HCID 100885762,6,7-trimethyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine

반응 조건

온도
45 °C

실험 절차

Anhydrous N,N-dimethylformamide (200 ml), anhydrous triethylamine (12.1 ml), and 2,4-dichloro-5,6-dimethyl-3-nitropyridine (16.05 g) were combined and 2-(3-pyridin-3-ylpropoxy)ethylamine (14.4 g) was then added with stirring. The pale yellow reaction mixture was heated to 45° C. under a nitrogen atmosphere for 1 hour. HPLC analysis indicated that the reaction was sufficiently complete to proceed. The reaction mixture was allowed to cool and the solvent was removed under reduced pressure. The resulting oil was dissolved in ethyl acetate and washed twice: once with a saturated aqueous solution of ammonium chloride and once with water. The organic layer was then extracted 3 times with brine, dried with magnesium sulfate, and concentrated under reduced pressure. The product was passed through a silica gel column using 90/10 ethyl acetate/hexane as the eluant. The resulting oil was dried under vacuum at 60° C. for 2 hours. NMR analysis indicated sufficient purity for use of the product in the next step.

후처리

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. washwashed twice
  5. extractionThe organic layer was then extracted 3 times with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was dried under vacuum at 60° C. for 2 hours

출처 및 근거

ORD 기록
ord-434969423a3c476c96a62fea7848db0f
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125890B2

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