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

HRID 623123Notes

Reaction equation

HRID 623123 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.CN>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:23][CH3:21])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 156171894-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143903972-(4-Fluorophenyl)-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamideYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.01845 mole) and 1,1'-carbonyldiimidazole (2.99 g, 0.01845 mole) was stirred at room temperature in dry tetrahydrofuran (100 ml) for three hours with a stream of nitrogen bubbling through it. A solution of methylamine in tetrahydrofuran (37 ml of a 3.03M solution, 0.111 mole) was added and the reaction mixture was stirred at room temperature under nitrogen overnight. The solvents were removed under reduced pressure and the residue was triturated in water (100 ml). The solid was collected by filtration, rinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, cooled to room temperature and isopropyl ether was added to the cloud point. The resulting solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at 42° C. overnight to give 2.30 g (44%) of title compound, mp. 215°- 217° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was triturated in water (100 ml)
  3. filtrationThe solid was collected by filtration
  4. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  5. dissolutionThe solid was dissolved in hot isopropyl alcohol
  6. filtrationfiltered hot
  7. temperaturecooled to room temperature
  8. additionisopropyl ether was added to the cloud point
  9. filtrationThe resulting solid was collected by filtration
  10. washrinsed with isopropyl ether
  11. customdried under high vacuum at 42° C. overnight

Sources & evidence

ORD record
ord-0f6db68665c442888abd69703dff1214
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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