Aniline → HCID 14390309, compound

HRID 2351697Notes

Reaction equation

HRID 2351697 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][CH: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][CH: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 6115AnilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390309HCID 14390309, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.6 g, 0.020 mole) was added dropwise (slowly) to a stirred and chilled (5°-10° C.) suspension of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (6.4 g, 0.019 mole) in anhydrous dimethylformamide (50 ml). The reaction mixture was heated at 55°-60° C. for 5 hours, cooled to room temperature, and added dropwise to a stirred and chilled (10°-15° C.) solution of aniline (1.9 g, 0.020 mole) and triethylamine (2.1 g, 0.020 mole) in anhydrous dimethylformamide (100 ml). The reaction mixture was stirred at room temperature overnight, filtered, and poured into ice water (500 ml). The mixture was allowed to precipitate and was filtered. The filter cake was triturated in potassium bicarbonate solution (100 ml), filtered, and the cake washed with water (100 ml). Recrystallization from tetrahydrofuran-isopropyl ether and then isopropyl alcohol-ethanol-tetrahydrofuran give 3.8 g (49%) of an off-white solid, mp 242°-243.5° C.

Workup

  1. temperaturechilled
  2. temperatureThe reaction mixture was heated at 55°-60° C. for 5 hours
  3. additionadded dropwise to
  4. stirringa stirred
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. filtrationfiltered
  7. additionpoured into ice water (500 ml)
  8. customto precipitate
  9. filtrationwas filtered
  10. customThe filter cake was triturated in potassium bicarbonate solution (100 ml)
  11. filtrationfiltered
  12. washthe cake washed with water (100 ml)
  13. customRecrystallization from tetrahydrofuran-isopropyl ether

Sources & evidence

ORD record
ord-6dc2a4f234df457ba98d387511103721
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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