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

HRID 623122Notes

Reaction equation

HRID 623122 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(N1C=CN=C1)([N:22]1C=CN=C1)=O.N>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[N:15]([CH2:16][C:17]([NH2:22])=[O:19])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 156171962-(5-methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143903962-(5-Methyl-2-thienyl)-3H-imidazo[4,5-b]pyridine-3-acetamideYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture 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) was stirred at room temperature in dry tetrahydrofuran (100 ml) for 2.5 hours with a stream of nitrogen bubbling through it. The reaction mixture was cooled in a dry ice/acetone bath, and liquid ammonia (50 ml) was added. The mixture was allowed to warm to room temperature and was stirred for 2 days under nitrogen atmosphere. The solvents were removed under reduced pressure and the resulting solid was triturated in water, collected by filtration, rinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. The solid was recrystallized from hot methanol and dried under high vacuum at 40° C. to give 2.82 g (56%) of title compound, mp>250° C.

Workup

  1. temperatureThe reaction mixture was cooled in a dry ice/acetone bath
  2. customThe solvents were removed under reduced pressure
  3. customthe resulting solid was triturated in water
  4. filtrationcollected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  6. customThe solid was recrystallized from hot methanol
  7. customdried under high vacuum at 40° C.

Sources & evidence

ORD record
ord-1a54d7a7af154193a7fcd4290e51e621
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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