Diethylamine → HCID 14390231, compound

HRID 621909Notes

Reaction equation

HRID 621909 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.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>O1CCCC1>[OH2:19].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])=[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 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390231HCID 14390231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.64 g, 0.020 mole) and 1,1'-carbonyldiimidazole (3.18 g, 0.02 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 2 hours with a stream of nitrogen bubbling through it. A solution of diethylamine (2.87 g, 0.04 mole) in tetrahydrofuran was added dropwise at room temperature to the stirred solution and the mixture was allowed to stir overnight. The tetrahydrofuran was evaporated and the solid residue was triturated with water. The solid was collected by filtration and dried under high vacuum overnight. The solid was recrystallized from isopropyl alcohol-water, collected by filtration, washed with water, and dried under high vacuum at room temperature over the weekend to give 3.83 g (57%) mp 155°-56° C.

Workup

  1. stirringto stir overnight
  2. customThe tetrahydrofuran was evaporated
  3. customthe solid residue was triturated with water
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum overnight
  6. customThe solid was recrystallized from isopropyl alcohol-water
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried under high vacuum at room temperature over the weekend
  10. customto give 3.83 g (57%) mp 155°-56° C.

Sources & evidence

ORD record
ord-ebbdae07fa1742bbb20d0aac2428b61c
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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