Methylamine → HCID 14390386, compound

HRID 2073085Notes

Reaction equation

HRID 2073085 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2(CC(O)=O)[NH:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[NH:8]2)=[CH:4][CH:3]=1.[C:20](N1C=CN=C1)([N:22]1[CH:26]=[CH:25]N=C1)=O.CN.[O:34]1CCCC1>>[Br:1][C:2]1[O:6][C:5]([C:7]2[N:15]([CH2:25][C:26]([NH:22][CH3:20])=[O:34])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 86742455HCID 86742455, compound

Product 1

HCID 14390386HCID 14390386, compoundYield 57%

Procedure

A suspension of 2-(5-bromo-2-furanyl)-3H-imidazo[4,5-b]pyridine acetic acid (5.0 g, 0.0155 mole) and 1,1'-carbonyldiimidazole (2.52 g, 0.0155 mole) in dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with a stream of nitrogen bubbling through it. A solution of methylamine in tetrahydrofuran (31 ml of a 3.03M solution, 0.093 mole) was added, and the suspension was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was evaporated under reduced pressure, and the residue was triturated in water. The resulting solid was collected by filtration and rinsed twice with water, twice with a 5% potassium hydroxide solution, and twice again with water. The solid was dissolved in hot isopropyl alcohol and filtered, and the solution was allowed to cool to room temperature. Addition of water caused a precipitate to form which was collected by filtration and dried under high vacuum to give 2.95 g (57%) of title compound, mp. 187°-191° C.

Workup

  1. stirringthe suspension was stirred at room temperature overnight under a nitrogen atmosphere
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue was triturated in water
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered
  8. temperatureto cool to room temperature
  9. additionAddition of water
  10. customto form which
  11. filtrationwas collected by filtration
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-4705814a7f9d4e339473f5183ebd11cb
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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