N-Methylpropylamine → HCID 23037339, compound

HRID 623102Notes

Reaction equation

HRID 623102 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.[CH3:33][NH:34][CH2:35][CH2:36][CH3:37]>O1CCCC1>[OH2:19].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:34]([CH3:33])[CH2:35][CH2:36][CH3:37])=[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 12315N-MethylpropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 23037339HCID 23037339, compoundYield 60%

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 2.5 hours with a stream of nitrogen bubbling through it. A solution of methylpropylamine (3.81 g, 0.0522 mole) in tetrahydrofuran (4 ml) was added, and the reaction mixture was heated at 45° C. for 15 hours, then stirred at room temperature. The solvents were evaporated under reduced pressure, and the resulting oil was triturated in water (100 ml) which caused a solid to form. The solid was collected by filtration and washed with water, twice with a 5% potassium hydroxide solution, and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered, and cooled to room temperature. Addition of water to the cloud point caused crystals to form. The solid was collected by filtration, rinsed with water, and dried at high vacuum to give 3.60 g (60%) of title compound, mp 130°-133° C.

Workup

  1. temperaturethe reaction mixture was heated at 45° C. for 15 hours
  2. stirringstirred at room temperature
  3. customThe solvents were evaporated under reduced pressure
  4. customthe resulting oil was triturated in water (100 ml) which
  5. customto form
  6. filtrationThe solid was collected by filtration
  7. washwashed with water, twice with a 5% potassium hydroxide solution
  8. dissolutionThe solid was dissolved in hot isopropyl alcohol
  9. filtrationfiltered
  10. temperaturecooled to room temperature
  11. additionAddition of water to the cloud point
  12. customto form
  13. filtrationThe solid was collected by filtration
  14. washrinsed with water
  15. customdried at high vacuum

Sources & evidence

ORD record
ord-6b89a0d222c143cca97d56e263201fd2
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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