Ammonium formate → HCID 10360094, compound

HRID 1168272Notes

Reaction equation

HRID 1168272 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]2[C:5]([C:12]([NH:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]2)=[O:13])=[CH:4][C:3]=1Cl.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]2[C:5]([C:12]([NH:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]2)=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10429706CJ-033466

Product 1

HCID 10360094HCID 10360094, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-amino-6-chloro-N-[(1-isobutylpiperidin-4-yl)methyl]-2-methylimidazo[1,2-a]pyridine-8-carboxamide (EXAMPLE 26, Step 6, 134 mg, 0.36 mmol), 10% palladium charcoal (67 mg) and ammonium formate (224 mg, 3.6 mmol) in methanol (5 mL ) was stirred at room temperature for 4 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was treated with 25% aqueous ammonia (10 mL), extracted with dichloromethane (20 mL×2) and washed with brine (20 mL). Removal of the solvent gave 92.4 mg (0.37 mmol, 76%) of the title compound as a yellow amorphous.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was treated with 25% aqueous ammonia (10 mL)
  4. extractionextracted with dichloromethane (20 mL×2)
  5. washwashed with brine (20 mL)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-eaef6be34bd7410896f5e2b7add56036
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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