Triethylamine → HCID 14390302, compound

HRID 2073020Notes

Reaction equation

HRID 2073020 reaction equation
C(Cl)(=O)C(Cl)=[O:3].[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:29]=[N:30][CH:31]=[CH:32][CH:33]=1.C(N(CC)CC)C>CN(C)C=O>[OH2:3].[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:29]=[N:30][CH:31]=[CH:32][CH:33]=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 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390302HCID 14390302, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (3.4 g, 0.0267 mole) was added dropwise (slowly) to a stirred and chilled (10° C.) solution of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (8.4 g, 0.0254 mole) in anhydrous dimethylformamide (50 ml). The reaction was heated at 55°-60° C. for 4 hrs, cooled to room temperature, and added dropwise to a stirred and chilled (10° C.) solution of 3-aminopyridine (2.6 g, 0.0279 mole) and triethylamine (5.4 g, 0.0534 mole) in anhydrous dimethylformamide (100 ml). The reaction mixture was stirred at room temperature overnight and then 100 ml of dimethylformamide was distilled off at 100 mm Hg. The residue was cooled and triturated in potassium bicarbonate solution (2×50 ml) and filtered. The filter cake was rinsed with water (2×50 ml) and recrystallized from isopropyl alcohol-isopropyl ether, giving 5.64 g (53%) of solids. Recrystallization from isopropyl alcoholisopropyl ether gave 2.3 g of an off-white solid, mp. 215°-217° C.

Workup

  1. temperatureThe reaction was heated at 55°-60° C. for 4 hrs
  2. additionadded dropwise to
  3. stirringa stirred
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. distillation100 ml of dimethylformamide was distilled off at 100 mm Hg
  6. temperatureThe residue was cooled
  7. customtriturated in potassium bicarbonate solution (2×50 ml)
  8. filtrationfiltered
  9. washThe filter cake was rinsed with water (2×50 ml)
  10. customrecrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-bcdd8041ee7340e68ca94f9759509f18
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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