Methylamine → N-Methyl-2-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetamide

HRID 622032Notes

Reaction equation

HRID 622032 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[N:15]([CH2:16][C:17]([OH:19])=O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=C1)=O.CN>O1CCCC1>[CH3:20][NH:22][C:17](=[O:19])[CH2:16][N:15]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 156171962-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390392N-Methyl-2-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0183 mole) and 1,1'-carbonyldiimidazole (2.97 g, 0.0183 mole) in tetrahydrofuran (100 ml) was stirred at room temperature for 33/4 hours with a stream of nitrogen bubbling through it. A solution of methylamine (36 ml of a 3.03M solution in tetrahydrofuran, 0.1098 mole) was added and the reaction mixture was stirred at room temperature overnight under nitrogen. The solvents were removed under reduced pressure and the resulting solid was triturated in water (100 ml), collected by filtration, and rinsed twice with water, twice with a 5% potassium hydroxide solution, and twice again with water. The solid was dissolved in hot isopropyl alcohol, and filtered while hot. Addition of isopropyl ether caused solid to precipitate. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at room temperature overnight to give 3.12 g (60%) of title compound, mp 213°-216° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe resulting solid was triturated in water (100 ml)
  3. filtrationcollected by filtration
  4. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  5. dissolutionThe solid was dissolved in hot isopropyl alcohol
  6. filtrationfiltered while hot
  7. additionAddition of isopropyl ether caused solid
  8. customto precipitate
  9. filtrationThe solid was collected by filtration
  10. washrinsed with isopropyl ether
  11. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-48e501d2eb634bb0a480c88db60c5094
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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