Chloroacetyl chloride → 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

HRID 1925473ノート

反応式

HRID 1925473 の反応式
[Cl:1][CH2:2][C:3](Cl)=O.[O:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][C:15]=2[NH2:24])[CH2:8][CH2:7]1>ClCCl>[Cl:1][CH2:2][C:3]1[N:13]([CH2:12][CH:9]2[CH2:8][CH2:7][O:6][CH2:11][CH2:10]2)[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1

参加物

4

反応物 2

HCID 6577Chloroacetyl chlorideHCID 69001829N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine

生成物 1

HCID 672629742-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline収率 88.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Chloroacetyl chloride (12 mL, 151 mmol) was dissolved in dichloromethane (30 mL) and added via addition funnel, over 20 minutes, to a stirring solution of N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (35.3 g, 137 mmol) in dichloromethane (300 mL). The resulting solution was stirred at ambient temperature under nitrogen for 24 hours at which point the solution was heated to 40° C. for an additional 24 hours. The mixture was cooled to ambient temperature, diluted with dichloromethane (150 mL) and transferred to a separatory funnel. The organic layer was washed with water (2×200 mL) and brine (2×200 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide 38.3 g of 2-(chloromethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline as a light brown solid.

後処理

  1. temperaturewas heated to 40° C. for an additional 24 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. customtransferred to a separatory funnel
  4. washThe organic layer was washed with water (2×200 mL) and brine (2×200 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-28dd932b72124973b4341820ff2664a9
出典データセット
uspto-grants-2012_05
特許番号
US08178677B2

反応ノート

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