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

HRID 622045Notes

Reaction equation

HRID 622045 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:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.N>O1CCCC1>[OH2:19].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH2:23])=[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 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 156171894-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143904012-(4-Fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide hydrateYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.49 g, 0.0166 mole) and 1,1'-carbonyldiimidazole (2.69 g, 0.0166 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 overnight under nitrogen. The solvents were removed under reduced pressure and the resulting solid was triturated in water (100 ml), 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 methanol, filtered while hot and cooled to room temperature. Water was added to the cloud point. The resulting solid was collected by filtration, rinsed with water, and dried under high vacuum at room temperature to give 3.04 g (68%) of title compound, mp. 246°-248° 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 (100 ml)
  4. filtrationcollected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  6. dissolutionThe solid was dissolved in hot methanol
  7. filtrationfiltered while hot and
  8. temperaturecooled to room temperature
  9. additionWater was added to the cloud point
  10. filtrationThe resulting solid was collected by filtration
  11. washrinsed with water
  12. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-491a1e0b51214bb88b1e32e02c774faf
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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