Ethyl Acetate → 5-[(diisobutylamino)methyl]-1-(3-{methyl[2-(2-pyridinyl)ethyl]amino}propyl)-N-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-2-amine

HRID 1727422노트

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HRID 1727422 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:11]([CH2:49][CH:50]([CH3:52])[CH3:51])[C:12]([C:14]1[CH:48]=[CH:47][C:17]2[N:18]([CH2:34][CH2:35][CH2:36][N:37]([CH3:46])[CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[C:19]([NH:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)=[N:20][C:16]=2[CH:15]=1)=O)[CH:8]([CH3:10])[CH3:9].C(OCC)(=O)C>O1CCCC1>[CH2:7]([N:11]([CH2:12][C:14]1[CH:48]=[CH:47][C:17]2[N:18]([CH2:34][CH2:35][CH2:36][N:37]([CH3:46])[CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[C:19]([NH:21][C:22]3[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=3)=[N:20][C:16]=2[CH:15]=1)[CH2:49][CH:50]([CH3:51])[CH3:52])[CH:8]([CH3:10])[CH3:9]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 10196994N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-5-carboxamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 575676335-[(diisobutylamino)methyl]-1-(3-{methyl[2-(2-pyridinyl)ethyl]amino}propyl)-N-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-2-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

A molar solution of lithium aluminium hydride in tetrahydrofuran (0.83 ml, 5 eq) is added dropwise to a solution of N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl) amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-5-carboxamide (105 mg, 1 eq. prepared according to Example A1) cooled down to 0° C., in tetrahydrofuran (3 ml). After stirring for 15 minutes at 0° C., the mixture is heated at 60° C. for 3 hours then cooled down to 0° C. and hydrolysed. After adding ethyl acetate, decanting and extraction, the combined organic phases are washed with salt water, followed by drying over sodium sulphate and concentrating under reduced pressure. Purification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1) produces the expected compound in the form of a foam (63 mg, 62% yield).

후처리

  1. temperaturethe mixture is heated at 60° C. for 3 hours
  2. temperaturethen cooled down to 0° C.
  3. customdecanting
  4. extractionextraction
  5. washthe combined organic phases are washed with salt water
  6. dry with materialby drying over sodium sulphate
  7. concentrationconcentrating under reduced pressure
  8. customPurification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)

출처 및 근거

ORD 기록
ord-33abe81a08544fd2ad1c5dcbb17a925d
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495110B2

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