Water → HCID 14390348, compound

HRID 2351783Notes

Reaction equation

HRID 2351783 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][CH2:24][C:25]([OH:27])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[CH3:28][N:29]([CH3:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1N.O.C[N:40](C)C=O>C(N(CC)CC)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][CH2:24][C:25]([NH:40][C:33]3[CH:34]=[CH:35][C:30]([N:29]([CH3:37])[CH3:28])=[CH:31][CH:32]=3)=[O:27])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 65578Oxalyl chlorideHCID 760831,2-Benzenediamine, N,N-dimethyl-HCID 15617213HCID 15617213, compound

Product 1

HCID 14390348HCID 14390348, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, oxalyl chloride (1.75 g, 0.0138 mole) was added dropwise, slowly, to a stirred and chilled (10° C.) suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-propanoic acid (4.0 g, 0.0133 mole) in anhydrous dimethylformamide (20 ml). A yellow solid formed. The suspension was stirred at room temperature for a few minutes and then a solution of N,N-dimethylphenylenediamine (2.0 g, 0.0147 mole) in dimethylformamide (25 ml) was added. The resulting purple solution was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was poured into 140 ml of water and stirred at room temperature. Triethylamine (2.0 ml) was added to pH 8 and a solid precipitated. The solid was collected by filtration, dissolved in hot isopropyl alcohol, treated with charcoal, and filtered. Addition of water and cooling to room temperature caused a solid to form. The solid was collected by filtration and rinsed with water to give 1.1 g of solid (20% yield). Drying under high vacuum at room temperature and then at 80° C. gave a grayish solid, mp 216°-218° C.

Workup

  1. temperaturechilled
  2. customA yellow solid formed
  3. stirringThe suspension was stirred at room temperature for a few minutes
  4. stirringThe resulting purple solution was stirred at room temperature overnight under a nitrogen atmosphere
  5. stirringstirred at room temperature
  6. customa solid precipitated
  7. filtrationThe solid was collected by filtration
  8. dissolutiondissolved in hot isopropyl alcohol
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. additionAddition of water
  12. customto form
  13. filtrationThe solid was collected by filtration
  14. washrinsed with water

Sources & evidence

ORD record
ord-c237d05bd8b94ea9b80343f9182119f4
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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