Ammonia → HCID 14390394, compound

HRID 2351768Notes

Reaction equation

HRID 2351768 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][CH2:18][C:19]([OH:21])=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:24]1C=CN=C1)=O.N>O1CCCC1.C(=O)=O.CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][CH2:18][C:19]([NH2:24])=[O:21])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 15617213HCID 15617213, compound

Product 1

HCID 14390394HCID 14390394, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Procedure

A mixture of 2(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-propanoic acid (5.52 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. Liquid ammonia (50 ml) was added to the reaction mixture (cooled in dry ice/acetone bath) and 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 2.86 g (52%) of title compound, mp. 248°-250° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe resulting solid was triturated in water (100 ml)
  3. filtrationcollected by filtration
  4. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  5. customThe solid was recrystallized from hot methanol
  6. customdried under high vacuum at 40° C.

Sources & evidence

ORD record
ord-b3c69686349f44f3b7dc71320bcb5469
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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