1,1'-Carbonyldiimidazole → HCID 23037392, compound

HRID 1709553Notes

Reaction equation

HRID 1709553 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: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)(N1C=CN=C1)=O.[NH2:33][CH:34]1[CH2:38][N:37]([CH2:39][CH3:40])[N:36]([CH2:41][CH3:42])[CH2:35]1>O1CCCC1>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:33][CH:34]3[CH2:38][N:37]([CH2:39][CH3:40])[N:36]([CH2:41][CH3:42])[CH2:35]3)=[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 5591991,2-Diethyl-4-pyrazolidinamineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 23037392HCID 23037392, compoundYield 118%

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 strired at room temperature for two hours with nitrogen bubbling through it. A solution of 4-amino-1,2-diethyl-pyrazolidine (7.5 g, 0.0522 mole) in tetrahydrofuran (6 ml) was added and the reaction mixture was stirred at room temperature overnight under nitrogen. The reaction mixture was evaporated under reduced pressure to an oil. Water (200 ml) was added, and the resulting suspension was stirred. The solid was 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 acidified with hydrogen chlorodie in isopropyl alcohol. Isopropyl ether was added to the cloud point, and upon cooling to room temperature, a solid precipitated. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum to give 4.8 g (56%) of title compound, mp 220° C. (darkens), 228°-230° C. (melts).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure to an oil
  2. additionWater (200 ml) was added
  3. stirringthe resulting suspension was stirred
  4. filtrationThe solid was collected 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. additionIsopropyl ether was added to the cloud point
  9. temperatureupon cooling to room temperature
  10. customa solid precipitated
  11. filtrationThe solid was collected by filtration
  12. washrinsed with isopropyl ether
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-a745a89e78ac4935a996b9eb59c6e161
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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