Ammonia → HCID 14390395, compound

HRID 2073106Notes

Reaction equation

HRID 2073106 reaction equation
[Br:1][C:2]1[O: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>[Br:1][C:2]1[O: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 14390458HCID 14390458, compound

Product 1

HCID 14390395HCID 14390395, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(5-bromo-2-furanyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.90 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 (100 ml), 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 2.23 g (38%) 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. customThe solid was recrystallized from hot methanol
  7. customdried under high vacuum at 40° C.

Sources & evidence

ORD record
ord-ada30ebc2d564a8cab0f4564b16ed0b1
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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