Triethylamine → 1-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-pyridyl)benzoyl]piperazine

HRID 379559노트

반응식

HRID 379559 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.C(N(CC)CC)C.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[Br:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42]([S:47]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)(=[O:49])=[O:48])[CH:41]=[CH:40]2>CN(C=O)C>[Br:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42]([S:47]([N:50]1[CH2:51][CH2:52][N:53]([C:11](=[O:13])[C:10]3[CH:9]=[CH:8][C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:15][CH:14]=3)[CH2:54][CH2:55]1)(=[O:48])=[O:49])[CH:41]=[CH:40]2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8216924-(2-Pyridyl)Benzoic AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 223297171-(6-Bromonaphth-2-ylsulphonyl)piperazine hydrochloride

생성물 1

HCID 223297521-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-pyridyl)benzoyl]piperazine수율 17.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(2-Pyridyl)benzoic acid (199 mg,1 mmol) was suspended in DMF (5 mL) and triethylamine (0.14 mL, 1 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes then cooled to 5° C. Carbonyl diimidazole (162 mg, 1 mmol) was added and the reaction mixture allowed to warm slowly to room temperature over one hour. 1-(6-Bromonaphth-2-ylsulphonyl)piperazine hydrochloride (393 mg, 1 mmol) was added as a solid in one portion and the reaction mixture was stirred overnight at room temperature then concentrated in vacuo. The crude product was dissolved in ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate solution (2×50 mL). The tube organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting off white solid was subjected to chromatography (SiO2; 100% EtOAc) to yield 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(2-pyridyl)benzoyl]piperazine as a white solid (92 mg); 1H NMR (DMSO-d6) δ=3.09 ppm (s,4H), δ=3.62 ppm (s,4H), δ=7.37 ppm (t,1H), δ=7.51 to 7.99 ppm (m,4H), δ=7.42 and 8.08 ppm (dd,4H), δ=8.17 ppm (dd,2H), δ=8.40 ppm (d,1H), δ=8.47 ppm (s,1H), δ=8.66 ppm (dd,1H); MS (M+H)+ 536.

후처리

  1. temperaturethen cooled to 5° C
  2. temperatureto warm slowly to room temperature over one hour
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. concentrationthen concentrated in vacuo
  5. dissolutionThe crude product was dissolved in ethyl acetate (50 mL)
  6. washwashed with aqueous sodium bicarbonate solution (2×50 mL)
  7. dry with materialThe tube organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a102949242da4bb9b1513820272ee208
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300330B1

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