Methylamine → HCID 14390226, compound

HRID 621905Notes

Reaction equation

HRID 621905 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:15]([CH2:16][C:17]([OH:19])=O)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1.[CH3:20][NH2:21]>O1CCCC1>[CH3:20][NH:21][C:17](=[O:19])[CH2:16][N:15]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15617180HCID 15617180, compound

Product 1

HCID 14390226HCID 14390226, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.44 g, 0.0096 mole, 1-1'-carbonyldiimidazole (1.56 g, 0.0096 mole), and anhydrous tetrahydrofuran (100 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 5 hours. A solution of 1M monomethylamine in tetrahydrofuran (15 ml) was added and the reaction stoppered and stirred overnight. The tetrahydrofuran was evaporated in vacuo and the residue triturated in water (30 ml) and filtered. The filter cake was again triturated in water (30 ml) and filtered, giving 1.94 g (76%) of solid, mp 228°-230° C. Recrystallization from tetrahydrofuran-methanol gave 1.49 g of a white solid, mp 228.5°-230° C.

Workup

  1. customThe tetrahydrofuran was evaporated in vacuo
  2. customthe residue triturated in water (30 ml)
  3. filtrationfiltered
  4. customThe filter cake was again triturated in water (30 ml)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bc198effeea540ad800555b609747087
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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