Ammonium formate → 5-AMINO-N-[(1-BUTYL-4-PIPERIDINYL)METHYL]IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE

HRID 1168246Notes

Reaction equation

HRID 1168246 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:16]2)=[O:12])=[CH:4][C:3]=1Cl.C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([NH:13][CH2:14][CH:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20]2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 102701115-amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloroimidazo[1,2-a]pyridine-8-carboxamide

Product 1

HCID 120880925-AMINO-N-[(1-BUTYL-4-PIPERIDINYL)METHYL]IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDEYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloroimidazo[1,2-a]pyridine-8-carboxamide (EXAMPLE 1, METHOD A, Step 5, 70 mg, 0.19 mmol), ammonium formate (120 mg, 1.9 mmol) and 10% palladium on carbon (50 mg) in methanol (5 mL) was stirred at room temperature under nitrogen atmosphere for 2 h. The mixture was filtered through a pad of Celite, and the filtrate was basified with 25% aqueous ammonia. This was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% aqueous ammonia (90:10:1) to give 40 mg (63%) of the title compound as a gum.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customThis was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% aqueous ammonia (90:10:1)

Sources & evidence

ORD record
ord-1663ca603b98484990236b574790dfb4
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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