Water → HCID 14390219, compound

HRID 2351646Notes

Reaction equation

HRID 2351646 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 at 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 at 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-102908a5fa824c4897a0f7e3bfcceafc
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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