3-Pyridineacetic acid → HCID 14390378, compound

HRID 2351750Notes

Reaction equation

HRID 2351750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=C([CH2:23][C:24](O)=[O:25])C=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:39][CH2:40][CH2:41][C:42]1[N:43]([CH3:47])[CH:44]=[CH:45][CH:46]=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:23][C:24]([NH:39][CH2:40][CH2:41][C:42]3[N:43]([CH3:47])[CH:44]=[CH:45][CH:46]=3)=[O:25])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1083-Pyridineacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 5650581-methyl-1H-pyrrole-2-ethylamineHCID 178477971HCID 178477971, compound

Product 1

HCID 14390378HCID 14390378, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine]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 3 hr with a stream of nitrogen bubbling through it. A solution of 2-(2-aminoethyl)-1-methylpyrrole (5.40 g, 0.0435 mole) in tetrahydrofuran (6 ml) was added and the mixture was stirred at room temperature under nitrogen overnight. The solvent was 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, rinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol and filtered hot. Water was added to the cloud point. Upon cooling, a solid precipitated which was collected by filtration, rinsed with water, and dried under high vacuum at 50° C. overnight to give 4.31 g (63%) of title compound, mp 171°-172.5° C.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting oil was triturated in water (100 ml) which
  4. customto form
  5. filtrationThe solid was collected by filtration
  6. washrinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. filtrationfiltered hot
  9. additionWater was added to the cloud point
  10. temperatureUpon cooling
  11. customa solid precipitated which
  12. filtrationwas collected by filtration
  13. washrinsed with water
  14. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-f5c0f380f2ba421abfc54e9551688745
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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