Triethylamine → HCID 23037419, compound

HRID 2351644Notes

Reaction equation

HRID 2351644 reaction equation
C(Cl)(=O)C(Cl)=[O:3].[Cl: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.O>[OH2:3].[Cl: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

7

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 65578Oxalyl chlorideHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 23037419HCID 23037419, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.41 g, 0.0190 mole) was added dropwise to a stirred suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.28 g, 0.0184 mole) in anhydrous dimethylformamide (70 ml). The resulting solution was stirred at room temperature for 3 hrs and was then added dropwise to a stirred and chilled (15°-20° C.) solution of 3-amino-pyridine (1.79 g, 0.0190 mole), triethylamine (1.92 g, 0.0190 mole) and dimethylformamide (30 ml). The reaction mixture was stirred at room temperature overnight and then poured into 300 ml of water. The mixture was filtered. The filter cake was suspended between methylene chloride (200 ml) and 5% sodium hydroxide (100 ml) and the methylene chloride was separated. The aqueous portion was extracted with methylene chloride (100 ml). The combined methylene chloride layers were washed with 5% sodium hydroxide (2×50 ml), water (50 ml), dried over sodium sulfate, and concentrated. The residue (4.3 g, 66%) was twice recrystallized from isopropyl alcohol-isopropyl ether to give 3.2 g of a white granular solid, mp 217°-218° C.

Workup

  1. additionwas then added dropwise to
  2. stirringa stirred
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. filtrationThe mixture was filtered
  5. customthe methylene chloride was separated
  6. extractionThe aqueous portion was extracted with methylene chloride (100 ml)
  7. washThe combined methylene chloride layers were washed with 5% sodium hydroxide (2×50 ml), water (50 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue (4.3 g, 66%) was twice recrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-f6d40f858f584c57af68d563e3ac4dde
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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