Triethylamine → 2-(4-{[(1E)-5-pyrimidin-2-ylpent-1-en-1-yl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine

HRID 1723806ノート

反応式

HRID 1723806 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH:10](O)[CH2:11][S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:23][N:22]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:22]=[CH:23][C:24]([O:27][CH2:28][C:29]([F:30])([F:31])[F:32])=[CH:25][N:26]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688486265-Pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-ol

生成物 1

HCID 688456502-(4-{[(1E)-5-pyrimidin-2-ylpent-1-en-1-yl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of the 5-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-ol (9.10 g, 18.6 mmol), triethylamine (13 mL, 93.0 mmol) in DCM (200 mL) at 0° C. was added methanesulfonyl chloride (2.16 mL, 27.9 mmol). The reaction was stirred at 0° C. for 15 minutes, warmed to room temperature and stirred for 16 hours. The reaction mixture was then washed with water (200 mL) and the aqueous back extracted with DCM (200 mL). The combined DCM extracts were washed with brine (250 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2-(4-{[(1E)-5-pyrimidin-2-ylpent-1-en-1-yl]sulfonyl}piperazin-1-yl)-5-(2,2,2-trifluoroethoxy)pyrimidine as an orange solid (8.79 g, 18.6 mmol, 100%).

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 hours
  3. washThe reaction mixture was then washed with water (200 mL)
  4. extractionthe aqueous back extracted with DCM (200 mL)
  5. washThe combined DCM extracts were washed with brine (250 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f5571aca91314f05b8c87a9e0131b7b3
出典データセット
uspto-grants-2009_02
特許番号
US07485644B2

反応ノート

読み込み中…