1-Pyrrolidineethanamine → HCID 22335171、化合物

HRID 586723ノート

反応式

HRID 586723 の反応式
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13](Cl)[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([NH:26][CH2:25][CH2:24][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 13441-PyrrolidineethanamineHCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

生成物 1

HCID 22335171HCID 22335171、化合物

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

Copper (II) sulphate (70 mg) was added to a solution of 6-benzyl-2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (0.75 g, 2.9 mmol)(WO9830560 Example 33 b) in 2-pyrrolidin-1-yl-ethylamine (3 ml) and the mixture was heated in an autoclave to 150° C. for 24 hours. The reaction mixture was cooled to room temperature and was diluted with dichloromethane (50 ml). The solution was washed with 50% ammonium hydroxide solution (50 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic solutions were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ammonium hydroxide and methanol in dichloromethane as eluant (gradient from 0.5:5:95 to 0.7:7:93) to give the title compound as a yellow oil (0.9 g). LRMS: m/z (ES+) 337 [MH+]

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe solution was washed with 50% ammonium hydroxide solution (50 ml)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane (2×50 ml)
  5. dry with materialThe combined organic solutions were dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-0c65a7d9b8264da78ff64c7c21ddd4df
出典データセット
uspto-grants-2005_08
特許番号
US06936619B2

反応ノート

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