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3-Amino-1-propanol → 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)amino]benzoate

HRID 1877497
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HRID 1877497 반응식
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:12]([C:14]1[N:19]=[CH:18][C:17]([C:20]2[C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([C:33]4[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[C:35](F)[CH:34]=4)[C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)#[N:13]>CS(C)=O.O>[C:12]([C:14]1[N:19]=[CH:18][C:17]([C:20]2[C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([C:33]4[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[C:35]([NH:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:34]=4)[C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)#[N:13]
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참가 물질

6

반응물 3

HCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 583382932-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate

생성물 1

HCID 673085942-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)amino]benzoate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 962
Water
용매

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온도
90 °C

실험 절차

0.9 g of potassium carbonate and 3.3 ml of 3-amino-1-propanol are successively added to a solution of 1 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate, obtained in stage 1 of Example 49, in 8 ml of dimethyl sulphoxide. The reaction mixture is heated at 90° C. for 1 and a half hours in a microwave, and then diluted with distilled water. The aqueous phase is washed twice with ethyl acetate and the combined organic phases are washed with water and a saturated solution of sodium chloride, dried over magnesium sulphate and filtered. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (70/30 by volume), so as to give 0.7 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxypropyl)-amino]benzoate in the form of a yellow oil, the characteristics of which are the following:

후처리

  1. washThe aqueous phase is washed twice with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. filtrationfiltered
  5. customThe residue is purified by silica gel chromatography, elution
  6. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (70/30 by volume)

출처 및 근거

ORD 기록
ord-ebb09d27b8ba48459ea290fed688b87f
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08309721B2

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