Water → 2-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

HRID 912760

반응식

HRID 912760 반응식
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.O>CS(C)=O>[Cl:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[C:17]=1[N:23]1[CH2:28][CH2:27][N:26]([C:2]2[NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:25][CH2:24]1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazoleHCID 114923451-(2,6-Dichlorophenyl)piperazine

생성물 1

HCID 100474472-[4-(2,6-Dichlorophenyl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of the benzoimidazole from step (c) above (75 mg, 0.34 mmol), the piperazine from step (a) above (90 mg, 0.39 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in DMSO (2 mL) was stirred at 80° C. for 24 h. The mixture was cooled to room temperature, water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (2×10 mL) and brine (5 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexane to give the title compound as a white solid. M.p. 263-265° C. MS (ESI, pos. ion) m/z: 415 (M+1).

후처리

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic phases were washed with water (2×10 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-d733d12a73de412484663657742d8122
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026241B2

연결된 노트

불러오는 중…