Water → HCID 178476585, 화합물

HRID 245767노트

반응식

HRID 245767 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178476589HCID 178476589, 화합물

생성물 1

HCID 178476585HCID 178476585, 화합물수율 93.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-baf218129b37482db90a5b1057f8da22
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

반응 노트

불러오는 중…