Carbon Dioxide → 1-[Butyl(methyl)amino]isoquinoline-7-carboxylic acid

HRID 14263

反応式

HRID 14263 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:12]([CH2:14][CH2:15][CH2:16][CH3:17])[CH3:13])=[CH:4][CH:3]=1.C([Li])(CC)C.[C:23](=[O:25])=[O:24].Cl>C(OCC)C>[CH2:14]([N:12]([CH3:13])[C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:23]([OH:25])=[O:24])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:15][CH2:16][CH3:17]

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 210859977-bromo-N-butyl-N-methylisoquinolin-1-amineHCID 178418400CID 53628100

生成物 1

HCID 210851781-[Butyl(methyl)amino]isoquinoline-7-carboxylic acid

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-60 °C

実験手順

To a −60° C. solution of 7-bromo-N-butyl-N-methylisoquinolin-1-amine (230 mg, 0.78 mmol) in diethyl ether was added sec-butyllithium (1.00 mL of a 1.3 M solution in cyclohexanes, 1.30 mmol). The solution was stirred at −60° C. for 20 min then excess dry ice (CO2) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The aqueous phase was concentrated under reduced pressure to yield a yellow oil. Purification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide) provided 1-[butyl(methyl)amino]isoquinoline-7-carboxylic acid (90 mg): ESI MS m/z 259 [M+H]+.

後処理

  1. temperatureto warm to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationThe aqueous phase was concentrated under reduced pressure
  4. customto yield a yellow oil
  5. customPurification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide)

出典と根拠

ORDレコード
ord-4d441e06c4224c11bed3d28739cb4527
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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