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

HRID 2068303ノート

反応式

HRID 2068303 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d8047ff79d924f9f8da2960c99d734e7
出典データセット
uspto-grants-2012_10
特許番号
US08293923B2

反応ノート

読み込み中…