Triethylamine → 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamide

HRID 1517319노트

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HRID 1517319 반응식
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([OH:13])=O.C(N(CC)CC)C.[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][NH:28][CH3:29]>O.O1CCCC1>[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([N:28]([CH2:27][CH2:26][CH2:25][N:24]([CH3:30])[CH3:23])[CH3:29])=[O:13]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 2479875,6-Dichloronicotinic acid

생성물 1

HCID 636953665,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamide수율 0.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
90 °C

실험 절차

Thionyl chloride (15 ml) was added to 5,6-dichloronicotinic acid (2.0 g, 10.4 mmol), and stirred under a nitrogen atmosphere at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure, and with cooling with ice, triethylamine (4.36 ml, 31.3 mmol) and N,N,N′-trimethylpropane-1,3-diamine (2.39 ml, 15.6 mmol) were added to a tetrahydrofuran solution (30 ml) of the obtained residue, and stirred at room temperature for 3 minutes. Saturated saline water was added to the reaction solution, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1) to obtain 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamide (3.21 mg) as an orange oil.

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. stirringstirred at room temperature for 3 minutes
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1)

출처 및 근거

ORD 기록
ord-1e66ed862a9f427783c27749ef41997f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232284B2

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