N,N'-Dimethylethylenediamine → HCID 70980214, 화합물

HRID 1749080노트

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HRID 1749080 반응식
[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

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 125101-Chloro-4-iodobenzeneHCID 25953Cesium fluorideHCID 70980205HCID 70980205, 화합물

생성물 1

HCID 70980214HCID 70980214, 화합물수율 87.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-440eb019f01946db917527e87d38a543
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09155743B2

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