1,1'-Carbonyldiimidazole → HCID 14390368, compound

HRID 2351740Notes

Reaction equation

HRID 2351740 reaction equation
[Cl: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)(N1C=CN=C1)=O.[NH2:33][CH2:34][CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH3:41]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:33][CH2:34][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][N:37]3[CH3:41])=[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 682631,1'-CarbonyldiimidazoleHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390368HCID 14390368, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. A solution of 2-(2-aminoethyl)-1-methylpyrrolidine (5.6 g, 0.0435 mole) in tetrahydrofuran (6 ml) was added and the reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere. The solvents were removed under reduced pressure. The resulting solid was triturated in water (200 ml), collected by filtration, rinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, and water was added. Upon cooling, a solid precipitated. The solid was collected by filtration and air dried to give 4.46 g (64%) of solid. A 0.5-g sample was dried under high vacuum to give 0.40 g of title compound, mp 170°-172° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere
  2. customThe solvents were removed under reduced pressure
  3. customThe resulting solid was triturated in water (200 ml)
  4. filtrationcollected by filtration
  5. washrinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. additionwater was added
  9. temperatureUpon cooling
  10. customa solid precipitated
  11. filtrationThe solid was collected by filtration and air
  12. customdried

Sources & evidence

ORD record
ord-976f153467f14c54b23915575f350ab9
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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