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Diisopropylethylamine → tert-Butyl[6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-propanoylpyridin-2-yl]carbamate

HRID 2088661
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HRID 2088661 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]([NH:27][CH2:28][CH2:29][NH2:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10]([NH:30][CH2:29][CH2:28][NH:27][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 57911766tert-Butyl (6-chloro-3-propanoylpyridin-2-yl)carbamate

생성물 1

HCID 57911744tert-Butyl[6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-propanoylpyridin-2-yl]carbamate

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매
HCID 962
Water
용매
HCID 8857Ethyl Acetate용매

실험 절차

730 mg (2.4 mmol) of tert-butyl(6-chloro-3-propanoylpyridin-2-yl)carbamate (Example 23A) were initially charged in 7 ml of DMSO, and 512 mg (3.2 mmol) of N-Boc-ethylenediamine and 640 μl (3.7 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous ammonium chloride solution and then with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). This gave 530 mg (53% of theory) of the product as a solid.

후처리

  1. customThe reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min
  2. washThe organic phase was washed with saturated aqueous ammonium chloride solution
  3. dry with materialwith saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1)

출처 및 근거

ORD 기록
ord-108d0b116d324d52b67783b3813635e6
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436003B2

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