Diisopropylcarbodiimide → methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate

HRID 1727415

反応式

HRID 1727415 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]=[C:12]=S)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(N=C=NC(C)C)(C)C.[NH2:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1)[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1>[CH3:30][O:29][C:27]([C:26]1[CH:31]=[CH:32][C:33]2[N:34]([CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[C:12]([NH:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)=[N:23][C:24]=2[CH:25]=1)=[O:28]

参加物

5

反応物 3

HCID 12734DiisopropylcarbodiimideHCID 1454223,5-Dimethoxyphenyl isothiocyanateHCID 69027376Methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate

生成物 1

HCID 69027642methyl-2-[(3,5-dimethoxyphenyl)amino]-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-1H-benzimidazole-5-carboxylate収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3,5 dimethoxyphenylisothiocyanate (571 mg, 1 eq) and diisopropylcarbodiimide (1.35 ml, 4 eq) are added successively to a solution of methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate (1.0 g, 1 eq) in tetrahydrofuran (10 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. The residue is taken up in ethyl acetate (100 ml) and water (40 ml). After decanting and extracting, the combined organic phases are washed with salt water, dried over Na2SO4 then evaporated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: dichloromethane/methanol 99:1 to 98:2) produces the expected compound in the form of a beige foam (1.12 g; 76% yield).

後処理

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. customAfter decanting
  5. extractionextracting
  6. washthe combined organic phases are washed with salt water
  7. dry with materialdried over Na2SO4
  8. customthen evaporated under reduced pressure at 40° C
  9. customPurification of the residue by flash chromatography on silica gel (eluent: dichloromethane/methanol 99:1 to 98:2)

出典と根拠

ORDレコード
ord-f1e39c8788fd45f9ac45d27ca0a27676
出典データセット
uspto-grants-2009_02
特許番号
US07495110B2

関連ノート

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