Triethylamine → 5,6-dichloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)nicotinamide

HRID 81676

반응식

HRID 81676 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][NH:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)(Cl)Cl.O.O1CCCC1>[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([N:24]([CH3:23])[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:13]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2479875,6-Dichloronicotinic acidHCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amine

생성물 1

HCID 551618625,6-dichloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)nicotinamide수율 102.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

Thionyl chloride (6 ml) was added to 5,6-dichloronicotinic acid (600 mg, 3.13 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 (1.31 ml, 9.38 mmol) and N-methyl-2-pyrrolidin-1-ylethanamine (481 mg, 3.75 mmol) were added to a tetrahydrofuran solution (4 ml) of the obtained residue, and stirred at room temperature for 3 minutes. Saturated saline water and chloroform were added to the reaction solution, 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-methyl-N-(2-pyrrolidin-1-ylethyl)nicotinamide 967 mg) as an orange oil.

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. stirringstirred at room temperature for 3 minutes
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. 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-b7936fa6667c445584f1ffe69e8e3eb8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

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