Ammonia → HCID 14390402, compound

HRID 2351776Notes

Reaction equation

HRID 2351776 reaction equation
[Br: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(N1C=CN=C1)([N:23]1C=CN=C1)=O.N>O1CCCC1>[Br: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 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390402HCID 14390402, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.51 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, and 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. The resulting solid was collected by filtration and dried under high vacuum at room temperature to give 3.00 g (54%) 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 (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. filtrationThe resulting solid was collected by filtration
  10. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-e9b1c8dcb0e3467f9c8e2488d31d04f4
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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