N,N'-Dimethylethylenediamine → HCID 89690318、化合物

HRID 2202848ノート

反応式

HRID 2202848 の反応式
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9](I)=[CH:8][N:7]3[C:13]=2[CH3:14])[CH2:3][CH2:2]1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][N:26]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:13]([CH3:14])=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:5]=3)[CH:8]=2)[C:25](=[O:29])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 896903982-Cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine

生成物 1

HCID 89690318HCID 89690318、化合物収率 55.6%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (1482 mg), 4-(benzyloxy)pyridin-2(1H)-one (1000 mg), copper iodide (946 mg), N,N′-dimethylethylenediamine (0.534 ml), potassium carbonate (2061 mg) and DMSO (13 ml) was heated 110° C. for 1 h under microwave irradiation. The residue was quenched with 28% NH3 solution, and extracted with EtOAc/THF. The organic layer was separated, washed with water and brine, dried over MgSO4, passed through silica gel pad (EtOAc only) and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/MeOH) and recrystallized from EtOH (80 ml) to give the title compound (1027 mg) as an off-white solid.

後処理

  1. customThe residue was quenched with 28% NH3 solution
  2. extractionextracted with EtOAc/THF
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/MeOH)
  8. customrecrystallized from EtOH (80 ml)

出典と根拠

ORDレコード
ord-5300e863aff94155984dad8898271339
出典データセット
uspto-grants-2016_06
特許番号
US09365540B2

反応ノート

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