Tetrahydrofuran → HCID 14390354, compound

HRID 621991Notes

Reaction equation

HRID 621991 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.O1CCCC1.[NH2:38][C:39]1[S:40][CH2:41][CH2:42][N:43]=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:38][C:39]3[S:40][CH2:41][CH2:42][N:43]=3)=[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

6

Reactant 4

HCID 8028TetrahydrofuranHCID 156894,5-Dihydro-2-thiazolamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390354HCID 14390354, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 with a stream of nitrogen bubbling through it. Solid 2-amino-2-thiazoline (2.67 g, 0.0261 mole) was added to the reaction mixture. The resulting suspension was allowed to stir at room temperature overnight. The solvent was evaporated under reduced pressure to give a white solid. The solid was triturated in water (200 ml), filtered, and the filter cake was rinsed twice more with water. The resulting solid was heated in boiling isopropyl alcohol to dissolve most of it, filtered while hot, and cooled to room temperature. A white precipitate formed. Water was added, and the white solid was filtered and rinsed once with isopropyl alcohol and twice with ispropyl ether. A 1.0-g sample of the resulting 3.3 g of white solid was dried at high vacuum to give 0.6 g (29%) of title compound, mp. 227°-229° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customto give a white solid
  4. customThe solid was triturated in water (200 ml)
  5. filtrationfiltered
  6. washthe filter cake was rinsed twice more with water
  7. temperatureThe resulting solid was heated
  8. dissolutionto dissolve most of it
  9. filtrationfiltered while hot, and
  10. temperaturecooled to room temperature
  11. customA white precipitate formed
  12. filtrationthe white solid was filtered
  13. washrinsed once with isopropyl alcohol and twice with ispropyl ether
  14. dry with materialA 1.0-g sample of the resulting 3.3 g of white solid was dried at high vacuum

Sources & evidence

ORD record
ord-0ad3df734ab7478c8f152a316ee6a535
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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