Phosphorus oxychloride → 8-Chloro-3-(1-methylpiperidin-4-yl)imidazo[1,5-a]pyrazine

HRID 245716ノート

反応式

HRID 245716 の反応式
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 86674656N-((3-chloropyrazin-2-yl)methyl)-1-methylpiperidine-4-carboxamide

生成物 1

HCID 866746578-Chloro-3-(1-methylpiperidin-4-yl)imidazo[1,5-a]pyrazine収率 91.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of N-((3-chloropyrazin-2-yl)methyl)-1-methylpiperidine-4-carboxamide (6.51 mmol, 1.75 g) in acetonitrile (10 ml) was added phosphorus oxychloride (65.1 mmol, 6.36 ml) and this solution was heated at 80° C. for four hours. The reaction mixture was concentrated in vacuo and coevaporated with toluene. The residue was cooled in an ice bath and quenched with 7N ammonia in methanol (50 ml) and dichloromethane (50 ml). The solids were removed by filtration and the filtrate was concentrated. To the residue dichloromethane (50 ml) and of 7N ammonia in methanol (1 ml) was added. After 10 minutes at room temperature the solids were removed by filtration and the filtrate was concentrated. To the residue dichloromethane (50 ml) was added. After 10 minutes at room temperature the solids were removed by filtration and the filtrate was concentrated to give 8-chloro-3-(1-methylpiperidin-4-yl)imidazo[1,5-a]pyrazine (1.5 g).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. temperatureThe residue was cooled in an ice bath
  3. customquenched with 7N ammonia in methanol (50 ml) and dichloromethane (50 ml)
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. additionTo the residue dichloromethane (50 ml) and of 7N ammonia in methanol (1 ml) was added
  7. customAfter 10 minutes at room temperature the solids were removed by filtration
  8. concentrationthe filtrate was concentrated
  9. additionTo the residue dichloromethane (50 ml) was added
  10. customAfter 10 minutes at room temperature the solids were removed by filtration
  11. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-db5e67fc968947a3ac4dec8674119d31
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

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