N,N'-Dimethylethylenediamine → HCID 70980214、化合物

HRID 1749080ノート

反応式

HRID 1749080 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[CH2:13][O:12][C:11]=2[N:17]=1.I[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.CNCCNC.[F-].[Cs+]>CC#N.[Cu]I>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([N:15]2[C:14](=[O:16])[CH2:13][O:12][C:11]3[N:17]=[C:7]([NH:6][CH2:5][C:4]4[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:3]=4[O:2][CH3:1])[CH:8]=[CH:9][C:10]2=3)=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 125101-Chloro-4-iodobenzeneHCID 25953Cesium fluorideHCID 70980205HCID 70980205、化合物

生成物 1

HCID 70980214HCID 70980214、化合物収率 87.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

6-(2,4-Dimethoxy-benzylamino)-1H-pyrido[2,3-b][1,4]oxazin-2-one (3.76 g, 11.9 mmol), 4-iodo-chlorobenzene (3.4 g, 14.3 mmol), N,N′-dimethylethylenediamine (1.27 mL, 11.9 mmol), and CsF (4.5 g, 29.7 mmol) were suspended in MeCN (100 mL) and sparged with nitrogen. CuI (238 mg, 1.19 mmol) was then added and the mixture stirred at 80° C. for 16 hours. The mixture was allowed to cool and was then concentrated in vacuo. The residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution. The EtOAc layer was then washed with saturated aqueous ammonium chloride solution, brine, dried over MgSO4, filtered and then concentrated in vacuo. The residue was purified using SiO2 chromatography (20-70% EtOAc/Petrol) to give 1-(4-chloro-phenyl)-6-(2,4-dimethoxybenzylamino)-1H-pyrido[2,3-b][1,4]oxazin-2-one (4.42 g) as a pale yellow crystalline solid. MS: [M+H]+=426.

後処理

  1. customsparged with nitrogen
  2. temperatureto cool
  3. concentrationwas then concentrated in vacuo
  4. customThe residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution
  5. washThe EtOAc layer was then washed with saturated aqueous ammonium chloride solution, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified

出典と根拠

ORDレコード
ord-440eb019f01946db917527e87d38a543
出典データセット
uspto-grants-2015_10
特許番号
US09155743B2

反応ノート

読み込み中…