Triethylamine → HCID 14390307, compound

HRID 1709505Notes

Reaction equation

HRID 1709505 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 65578Oxalyl chlorideHCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390307HCID 14390307, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (3.4 g, 0.027 mole) was added dropwise (slowly) to a stirred and chilled (10° C.) suspension of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (8.4 g, 0.025 mole) in anhydrous dimethylformamide (50 ml). The reaction mixture was heated at 55°-60° C. for 4 hours, cooled to room temperature, and added dropwise to a stirred and chilled (10° C.) solution of 2-aminopyridine (2.6 g, 0.028 mole) and triethylamine (5.4 g, 0.0053 mole) in anhydrous dimethyl formamide (100 ml). The reaction was stirred at room temperature overnight. Dimethylformamide (100 ml) was distilled off at 100 mm Hg. The residue was cooled, triturated in potassium bicarbonate solution (2×50 ml), and filtered. The filter cake was rinsed with water (2×50 ml) and recrystallized from ethanol-isopropyl ether to give 4.8 g (47%) of white solid, mp. 191.5°-195° C.

Workup

  1. temperaturechilled
  2. temperatureThe reaction mixture was heated at 55°-60° C. for 4 hours
  3. additionadded dropwise to
  4. stirringa stirred
  5. stirringThe reaction was stirred at room temperature overnight
  6. distillationDimethylformamide (100 ml) was distilled off at 100 mm Hg
  7. temperatureThe residue was cooled
  8. customtriturated in potassium bicarbonate solution (2×50 ml)
  9. filtrationfiltered
  10. washThe filter cake was rinsed with water (2×50 ml)
  11. customrecrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-591ce9f537b04d3a8859dd5f24def519
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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