Nitrogen → 8-Chloro-3-cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

HRID 449026ノート

反応式

HRID 449026 の反応式
N#N.[Cl:3][C:4]1[C:5]([CH:10]([NH:24][C:25]([CH:27]2[CH2:29][CH2:28]2)=O)[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][N:9]=1.CC#N.CN(C=O)C.O=P(Cl)(Cl)Cl>O>[Cl:3][C:4]1[C:5]2[N:6]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[N:24][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1

参加物

7

反応物 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 86636029Cyclopropanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide

生成物 1

HCID 866360288-Chloro-3-cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In an oven-dried flask filled with N2 was added cyclopropanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide (55 mg, 0.00014 mol), MeCN (4 mL, 0.07 mol) and DMF (0.7 mL, 0.009 mol). POCl3 was added dropwise at 0° C. The reaction mixture was warmed up to rt and stirred at that temperature overnight. The excess of POCl3 was removed under reduced pressure and the residue was quenched with solution of NH3 in i-PrOH (2 N) at 0° C. with vigorous stirring to adjust pH to 9. The crude reaction mixture was then charged with water and the aqueous layer was washed with DCM. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound, which was used in next step without further purification.

後処理

  1. customThe excess of POCl3 was removed under reduced pressure
  2. customthe residue was quenched with solution of NH3 in i-PrOH (2 N) at 0° C.
  3. stirringwith vigorous stirring
  4. customThe crude reaction mixture
  5. washthe aqueous layer was washed with DCM
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-12dfae03fb294ba9b6848bcf26992516
出典データセット
uspto-grants-2013_07
特許番号
US08481733B2

反応ノート

読み込み中…