Thiazolidine → HCID 14390359, compound

HRID 621994Notes

Reaction equation

HRID 621994 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.[S:33]1[CH2:37][CH2:36][NH:35][CH2:34]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18](=[O:20])[N:35]3[CH2:36][CH2:37][S:33][CH2:34]3)[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 10444ThiazolidineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390359HCID 14390359, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 3.5 hours while nitrogen was bubbled through it. Solid thiazolidine (2.33 g, 0.0261 mole) was added and the reaction mixture was stirred at 55° C., under nitrogen overnight. The solvent was removed under reduced pressure. The resulting white solid was triturated with water (100 ml), filtered, rinsed with water, twice with 5% potassium hydroxide solution and twice more with water. The resulting solid was heated in boiling isopropyl alcohol and filtered hot. Upon cooling to room temperature, a white solid precipitated. The solid was collected by filtration and dried under high vacuum to give 3.08 g (49.4%) of title compound, mp. 215°-218° C.

Workup

  1. customwas bubbled through it
  2. stirringthe reaction mixture was stirred at 55° C., under nitrogen overnight
  3. customThe solvent was removed under reduced pressure
  4. customThe resulting white solid was triturated with water (100 ml)
  5. filtrationfiltered
  6. washrinsed with water, twice with 5% potassium hydroxide solution and twice more with water
  7. temperatureThe resulting solid was heated
  8. filtrationfiltered hot
  9. temperatureUpon cooling to room temperature
  10. customa white solid precipitated
  11. filtrationThe solid was collected by filtration
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-a7b87471febe438e8729b49487f7d4f6
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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