Triethylsilane → N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine

HRID 2381223노트

반응식

HRID 2381223 반응식
[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=[N:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:40][N:2]([CH3:1])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])=[CH:5][CH:4]=1.[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 67026330(4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol

생성물 2

HCID 25004152N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine수율 32%HCID 57965652(4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanol수율 25%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of (4) (3.35 g, 6.40 mmol) in TFA (30 mL) was added triethylsilane (6 mL, 38.4 mmol). The reaction mixture was stirred at room temperature overnight. TFA was removed under vacuum. The residue was basified with 2 M sodium hydroxide to pH>7. The aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane to give N,N-dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine (5) (0.55 g, 2.07 mmol, 32% yield), and (4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanol (6) (0.45 g, 1.60 mmol, 25% yield).

후처리

  1. customTFA was removed under vacuum
  2. extractionThe aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane

출처 및 근거

ORD 기록
ord-5315613ac0324a558f2e79c9bf8dd180
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258167B2

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