Triethylamine → HCID 178519684, 화합물

HRID 42293

반응식

HRID 42293 반응식
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[NH:16][CH:17]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=1>O1CCCC1.O>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([CH:18]4[CH2:23][CH2:22][N:21]([C:31]([C:32]5[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=5)=[O:38])[CH2:20][CH2:19]4)[NH:16][CH:17]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 178420149HCID 178420149, 화합물

생성물 1

HCID 178519684HCID 178519684, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution of 2-phenyl-5-(2-(piperidin-4-yl)-1H-imidazol-4-yl)pyrimidine (76 mg, 0.25 mmol) in tetrahydrofuran (4 mL) was added triethylamine (51 mg, 0.50 mmol) followed by nicotinoyl chloride (49 mg, 0.27 mmol) and the reaction mixture was stirred for 1 hour at 0° C. then allowed to warm to room temperature. The reaction was diluted with water and the organic material extracted three times with ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude solid was chromatographed on silica (4 g) and eluted with ethanol-ethyl acetate to give the title compound as a solid; melting point 234° C.; Rf 0.31 with 0.5/10/40/50 acetic acid-isopropanol-hexane-dichloromethane; MS (ESI+) m/z 411 (M+1); H-PGDS FPBA IC50: 0.45 μM.

후처리

  1. temperatureto warm to room temperature
  2. extractionthe organic material extracted three times with ethyl acetate
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude solid was chromatographed on silica (4 g)
  7. washeluted with ethanol-ethyl acetate

출처 및 근거

ORD 기록
ord-0a62ec4288e441fda7acda4be64bb374
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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