Triethylamine → HCID 70926682, compound

HRID 240482Notes

Reaction equation

HRID 240482 reaction equation
N1([C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[CH3:13])C2C=CC=CC=2N=N1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1.CCN(CC)CC>C1COCC1>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[C:10](=[O:15])[CH2:11][C:12]([CH3:14])([CH3:13])[NH:24]2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115356995-Bromo-2-hydrazinopyridineHCID 267930961-(1H-1,2,3-Benzotriazol-1-yl)-3-methylbut-2-en-1-one

Product 1

HCID 70926682HCID 70926682, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(400 mg, 2.0 mmol) 1-Benzotriazol-1-yl-3-methyl-but-2-en-1-one (Example 1, step 1), (5-bromo-pyridin-2-yl)-hydrazine (410 mg, 2.2 mmol, 1.1 equiv.) and Et3N (1.95 ml, 14.0 mmol, 7 equiv.) were dissolved together in THF (2 ml) and stirred for 90 minutes at reflux temperature. The reaction mixture was cooled and extracted with saturated Na2CO3 solution and two times with ethyl acetate. The organic extracts were extracted with brine, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:cyclohexane gradient 0:100 to 50:50. The desired 2-(5-bromo-pyridin-2-yl)-5,5-dimethyl-pyrazolidin-3-one (230 mg, 43% yield) was obtained as a yellow oil, MS: m/e=270.2/272.2 (M+H+).

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with saturated Na2CO3 solution and two times with ethyl acetate
  4. extractionThe organic extracts were extracted with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe crude product was purified by flash chromatography on a silica gel column
  8. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-aa98d484574841e78f8d70938ba2a81f
Source dataset
uspto-grants-2014_02
Patent number
US08648088B2

Reaction notes

Loading…