Dimethylformamide → HCID 14390452, compound

HRID 2351785Notes

Reaction equation

HRID 2351785 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([OH:21])=O)[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:22][N:23](C)C=O.S(Cl)(Cl)=O.CN>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([NH:23][CH3:22])=[O:21])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 15097588HCID 15097588, compound

Product 1

HCID 14390452HCID 14390452, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of 5-chloro-2-(4-methylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.8 g, 0.0093 mole) in tetrahydrofuran (11.3 ml) and dimethylformamide (0.68 g, 0.0093 mole) was cooled in an ice bath under nitrogen. Thionyl chloride (1.22 g, 0.0102 mole) was added dropwise to the stirred suspension. After stirring at room temperature for twenty minutes, the solution was cooled again in an ice bath and a solution of methylamine in tetrahydrofuran (21.5 ml of a 2.59M solution, 0.056 mole) was added dropwise. The suspension was stirred at room temperature under nitrogen for one hour and then the solvents were removed under reduced pressure. The residue was triturated in water (100 ml) and the resulting solid was collected by filtration and rinsed three times with water. The solid was dissolved in hot isopropyl alcohol, filtered while hot, and brought to the cloud point with isopropyl ether. Upon cooling, a solid precipitated which was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at 70° C. to give 1.86 g(64% yield) of title compound, mp >250° C.

Workup

  1. temperaturethe solution was cooled again in an ice bath
  2. stirringThe suspension was stirred at room temperature under nitrogen for one hour
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated in water (100 ml)
  5. filtrationthe resulting solid was collected by filtration
  6. washrinsed three times with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. filtrationfiltered while hot, and
  9. temperatureUpon cooling
  10. customa solid precipitated which
  11. filtrationwas collected by filtration
  12. washrinsed with isopropyl ether
  13. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-43e777087e0d40bba8568770bed2ea75
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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