Acetonitrile → HCID 86704211、化合物

HRID 624030ノート

反応式

HRID 624030 の反応式
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Cl[CH2:10][C:11]([NH:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][N:15]=1)=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>C(Cl)Cl>[CH3:21][O:20][C:18]1[C:17]([O:22][CH3:23])=[CH:16][N:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)[N:19]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 68283152HCID 68283152、化合物

生成物 1

HCID 86704211HCID 86704211、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A flask was charged with 4-nitro-1H-pyrazole (A) (317 mg, 2.8 mmol), 2-chloro-N-(4,5-dimethoxypyrimidin-2-yl)acetamide (2.26 mmol), Cs2CO3 (1.0 g, 3.09 mmol) and MeCN (9.0 mL). The resulting reaction mixture was stirred at reflux (80° C.) for 1 h, then allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM. The filtercake was redisolved in DCM and water, the org. layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and concentrated to yield N-(4,5-dimethoxypyrimidin-2-yl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide as a crude which was used in the next step without further purification. LC-MS conditions B: tR=0.46 min, [M+H]+=309.10.

後処理

  1. customThe resulting reaction mixture
  2. customto reach rt
  3. filtrationfiltered
  4. washthe filter cake was washed with DCM
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with DCM (2×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-4a9573990c0843c6bdfd8fc2e11877eb
出典データセット
uspto-grants-2016_04
特許番号
US09303023B2

反応ノート

読み込み中…