Triethylamine → HCID 178519684, compound

HRID 42293

Reaction equation

HRID 42293 reaction equation
[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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 178420149HCID 178420149, compound

Product 1

HCID 178519684HCID 178519684, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a62ec4288e441fda7acda4be64bb374
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Linked notes

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