Methylamine → 2(3-Chlorophenyl)-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride

HRID 622988Notes

Reaction equation

HRID 622988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.CN>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143902292(3-Chlorophenyl)-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.89 g, 0.010 mole), 1,1'-carbonyldiimidazole (1.62 g, 0.010 mole), and anhydrous tetrahydrofuran (125 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 41/2 hours. A solution of 1M methylamine in tetrahydrofuran (15 ml, 0.015 mole) was added and the resulting solution was stoppered and stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue triturated twice in water (2×75 ml) and filtered. The filter cake (mp 186°-189° C.) was dissolved in isopropyl alcohol and treated with excess ethereal hydrogen chloride, giving 1.6 g (47%) of a white flocculent solid which melted from 195°-199° C. after a few crystals had melted between 185°-190° C. It was also observed that prolonged heating decreases the melting point.

Workup

  1. stirringstirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue triturated twice in water (2×75 ml)
  4. filtrationfiltered
  5. dissolutionThe filter cake (mp 186°-189° C.) was dissolved in isopropyl alcohol
  6. additiontreated with excess ethereal hydrogen chloride
  7. customgiving 1.6 g (47%) of a white flocculent solid which
  8. custommelted from 195°-199° C.
  9. customhad melted between 185°-190° C
  10. temperaturethat prolonged heating

Sources & evidence

ORD record
ord-8e0603c7e12f47bba448ae6cc993888e
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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