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

HRID 883688

반응식

HRID 883688 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e50e5f5eb4b64e4e9d1729119a561606
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236965B2

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