Triethylamine → HCID 14390380, compound

HRID 2351751Notes

Reaction equation

HRID 2351751 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.Cl.Cl.[CH3:29][N:30]([CH3:38])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=1.C(N(CC)CC)C>CN(C)C=O>[OH2:3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([NH:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([N:30]([CH3:38])[CH3:29])[CH:32]=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 65578Oxalyl chloride2×HCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390380HCID 14390380, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.03 g, 0.016 mole) was added dropwise, slowly, to a stirred and chilled solution of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole) in dry dimethylformamide (60 ml). The reaction mixture was stirred at room temperature for 1.5 hr, and then an additional 0.3 ml of oxalyl chloride was added. After stirring for an additional 0.5 hr, the solution was added dropwise to a stirred mixture of N,N-dimethyl-1,3-benzenediamine dihydrochloride (3.35 g, 0.016 mole) and triethylamine (6.46 g, 0.064 mole) in dimethylformamide (130 ml). The resultant mixture was stirred at room temperature overnight and poured into 400 ml of ice water. The solid which precipitated was collected by filtration, dissolved in hot isopropyl alcohol, and filtered hot. Upon cooling to room temperature, solid precipitated. Water was added and the solid was collected by filtration and rinsed with water. A 0.5 g sample was dried under high vacuum at room temperature to give 0.34 g of title compound, mp 215°-217° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.5 hr
  2. stirringAfter stirring for an additional 0.5 hr
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in hot isopropyl alcohol
  6. filtrationfiltered hot
  7. customsolid precipitated
  8. additionWater was added
  9. filtrationthe solid was collected by filtration
  10. washrinsed with water
  11. customA 0.5 g sample was dried under high vacuum at room temperature

Sources & evidence

ORD record
ord-33032fb3a98e465f822412564a1cce17
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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