Water → HCID 14390219, compound

HRID 2072967Notes

Reaction equation

HRID 2072967 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:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.CN.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:23][CH3:21])=[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 962WaterHCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390219HCID 14390219, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, a suspension of 2-(4-chlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acid, 6.0 g (0.021 mole) and 1,1'-carbonyldiimidazole (3.39 g, 0.021 mole) in tetrahydrofuran (150 ml) was refluxed, with stirring, for 2.5 hrs. The mixture was cooled to room temperature and a solution of 3.6 g (0.116 mole) of monomethylamine in tetrahydrofuran (60 ml) was added dropwise and the reaction mixture was stirred in room temperature overnight. The tetrahydrofuran was evaporated and the residue was triturated in water (150 ml). The solid was filtered and rinsed with water. The solid was dissolved in hot isopropyl alcohol, treated with charcoal, filtered, and allowed to cool. Solid formed, and water was added to precipitate more. The solid was filtered and dried under vacuum to give 3.0 g (47.5%) of title compound, mp 238°-238.5° C.

Workup

  1. temperaturewas refluxed
  2. stirringthe reaction mixture was stirred in room temperature overnight
  3. customThe tetrahydrofuran was evaporated
  4. customthe residue was triturated in water (150 ml)
  5. filtrationThe solid was filtered
  6. washrinsed with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. temperatureto cool
  11. customSolid formed
  12. customto precipitate more
  13. filtrationThe solid was filtered
  14. customdried under vacuum

Sources & evidence

ORD record
ord-5f4b2bd41ead49b780a9929bda8f298b
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

Loading…