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

HRID 1517315ノート

反応式

HRID 1517315 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08749f339c7d43c396e39bb3178fb5c4
出典データセット
uspto-grants-2012_07
特許番号
US08232284B2

反応ノート

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