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

HRID 1723806노트

반응식

HRID 1723806 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f5571aca91314f05b8c87a9e0131b7b3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485644B2

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