Methylamine → HCID 14390383, compound

HRID 1709568Notes

Reaction equation

HRID 1709568 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][C:20]([OH:22])=O)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23](N1C=CN=C1)([N:25]1C=CN=C1)=O.CN>O1CCCC1>[CH3:23][NH:25][C:20](=[O:22])[CH2:19][N:18]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390459HCID 14390459, compound

Product 1

HCID 14390383HCID 14390383, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of crude 2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.0 g, 0.0101 mole), 1,1'-carbonyldiimidazole (1.63 g, 0.0101 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for three hours with a stream of nitrogen bubbling through it and then refluxed overnight under nitrogen. It was cooled to room temperature and a solution of methylamine (0.94 g, 0.0302 mole) in tetrahydrofuran (10 ml) was added and the reaction mixture was stirred at room temperature over the weekend. The solvents were removed under reduced pressure and the resulting solid was triturated in water, collected by filtration, rinsed once with water, once with 5% potassium hydroxide solution and once with water. The solid was dissolved in hot isopropyl alcohol, filtered hot and cooled in the refrigerator to precipitate a solid. Water was added and the solid was collected by filtration and dried under high vacuum at 70° C. to give 0.42 g (13%) of title compound, mp. >260° C.

Workup

  1. temperaturerefluxed overnight under nitrogen
  2. temperatureIt was cooled to room temperature
  3. stirringthe reaction mixture was stirred at room temperature over the weekend
  4. customThe solvents were removed under reduced pressure
  5. customthe resulting solid was triturated in water
  6. filtrationcollected by filtration
  7. washrinsed once with water, once with 5% potassium hydroxide solution and once with water
  8. dissolutionThe solid was dissolved in hot isopropyl alcohol
  9. filtrationfiltered hot
  10. temperaturecooled in the refrigerator
  11. customto precipitate a solid
  12. additionWater was added
  13. filtrationthe solid was collected by filtration
  14. customdried under high vacuum at 70° C.

Sources & evidence

ORD record
ord-4bd4f4a81ca64c019af813b2c47cf76c
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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