Propylamine → HCID 14390236, compound

HRID 2351656Notes

Reaction equation

HRID 2351656 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.[CH2:33]([NH2:36])[CH2:34][CH3:35]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:36][CH2:33][CH2:34][CH3:35])=[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 7852PropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390236HCID 14390236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid 5.0 g (0.0174 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 2.5 hrs with a stream of nitrogen bubbling through it. The n-propylamine (2.06 g, 0.0348 mole) was added dropwise and the reaction mixture was allowed to stir at room temperature under nitrogen atmosphere overnight. The tetrahydrofuran was evaporated and the residue was triturated with water. The solid was collected and dried under high vacuum at 50° C. overnight. The solid was dissolved in isopropyl alcohol, filtered, diluted with water, and placed in the freezer overnight. The crystalline precipitate was collected by filtration, washed with water, and dried at 50° C. under high vacuum overnight to give 3.6 g (63%), m.p. 200°-21° C.

Workup

  1. stirringto stir at room temperature under nitrogen atmosphere overnight
  2. customThe tetrahydrofuran was evaporated
  3. customthe residue was triturated with water
  4. customThe solid was collected
  5. customdried under high vacuum at 50° C. overnight
  6. dissolutionThe solid was dissolved in isopropyl alcohol
  7. filtrationfiltered
  8. additiondiluted with water
  9. customplaced in the freezer overnight
  10. filtrationThe crystalline precipitate was collected by filtration
  11. washwashed with water
  12. customdried at 50° C. under high vacuum overnight
  13. customto give 3.6 g (63%), m.p. 200°-21° C.

Sources & evidence

ORD record
ord-8d08518f87d0419bbdd82bd51324a52f
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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