Imidazole → 5-((tert-butyldimethylsilyloxy)methyl)-1-cyclohexyl-1H-benzo[d]imidazol-2-amine

HRID 2068303노트

반응식

HRID 2068303 반응식
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:4]=2[N:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[Si:24]([O:18][CH2:17][C:15]1[CH:14]=[CH:13][C:5]2[N:6]([CH:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]3)[C:2]([NH2:1])=[N:3][C:4]=2[CH:16]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67252967(2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol

생성물 1

HCID 672543375-((tert-butyldimethylsilyloxy)methyl)-1-cyclohexyl-1H-benzo[d]imidazol-2-amine수율 56.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2-Amino-1-cyclohexyl-1H-benzoimidazol-5-yl)methanol (0.650 g, 0.00265 mol) and 1H-Imidazole (0.4149 g, 0.006094 mol) in N,N-Dimethylformamide (10 mL) was added tert-Butyldimethylsilyl chloride (0.4393 g, 0.002914 mol) and the mixture stirred for 1 hour. The mixture was diluted with ethyl acetate, washed with saturated socium bicarbonate, dried and concentrated. The residue was taken up in methylene chloride containing 0.1% triethylamine and purified by flash chromatography with a gradient of from 0 to 10 percent methanol. The product fractions were concentrated to give 539 mg of the product.

후처리

  1. washwashed with saturated socium bicarbonate
  2. customdried
  3. concentrationconcentrated
  4. custompurified by flash chromatography with a gradient of from 0 to 10 percent methanol
  5. concentrationThe product fractions were concentrated

출처 및 근거

ORD 기록
ord-d8047ff79d924f9f8da2960c99d734e7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293923B2

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