Ammonia → HCID 14390425, compound

HRID 2351775Notes

Reaction equation

HRID 2351775 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[C:18](O)=[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:24]1C=CN=C1)=O.N>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[C:18]([NH2:24])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 14390427(S)-2-(4-chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390425HCID 14390425, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-(4-Chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.65 g, 0.012 mole) and 1,1'-carbonyldiimidazole (1.96 g, 0.0121 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, 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 partitioned between water (100 ml) and ethyl acetate (100 ml). The insoluble solid was collected by filtration (1.38 g). The layers were separated, the aqueous layer was extracted once with ethyl acetate and the combined organic layers were washed twice with water, twice with a 5% potassium hydroxide solution and twice again with water, dried over magnesium sulfate, treated with charcoal, filtered, and evaporated under reduced pressure to gibe 1.9 g of solid. The 3.28 g (91 % yield) of solids were combined and dissolved in hot methanol, filtered hot, cooled to room temperature and 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 2.50 g of title compound, mp. 202°-204° 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 partitioned between water (100 ml) and ethyl acetate (100 ml)
  4. filtrationThe insoluble solid was collected by filtration (1.38 g)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted once with ethyl acetate
  7. washthe combined organic layers were washed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  8. dry with materialdried over magnesium sulfate
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-51aeab35036f4348a67ff96ed3afddba
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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