Water → HCID 178476585、化合物

HRID 245767ノート

反応式

HRID 245767 の反応式
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.O>CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([Br:21])[N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178476589HCID 178476589、化合物

生成物 1

HCID 178476585HCID 178476585、化合物収率 93.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To (cis)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (46.8 mmol, 12.8 g) in N,N-dimethylformamide (100 ml) was added N-bromosuccinimide (46.8 mmol, 8.33 g). After stirring at room temperature for one hour the reaction mixture was poured into water and extracted with dichloromethane twice. The combined organic layers were washed with water twice, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 3% of methanol) to give (cis)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (15.34 g).

後処理

  1. extractionextracted with dichloromethane twice
  2. washThe combined organic layers were washed with water twice
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 3% of methanol)

出典と根拠

ORDレコード
ord-baf218129b37482db90a5b1057f8da22
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

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