Ammonium formate → HCID 178464891, compound

HRID 2246628Notes

Reaction equation

HRID 2246628 reaction equation
[CH2:1]([NH:3][C:4](=[O:28])[C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=4)=[N:16][NH:17]3)=[CH:13][CH:12]=2)[C:8]([CH3:26])=[C:7]([F:27])[CH:6]=1)[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:1]([NH:3][C:4](=[O:28])[C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)=[N:16][NH:17]3)=[CH:13][CH:12]=2)[C:8]([CH3:26])=[C:7]([F:27])[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58899619HCID 58899619, compound2×

Product 1

HCID 178464891HCID 178464891, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-ethyl-3-fluoro-4-methyl-5-[3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indazol-6-yl]benzamide (Intermediate 21, 100 mg), 10% palladium on carbon (20 mg) and ammonium formate (50 mg) in ethanol (10 mL) was stirred at 90° C. for 1 h under nitrogen. The catalyst was removed by filtration and the filtrate was concentrated under vacuum. The product was dissolved in methanol and eluted through an SCX ion exchange cartridge. Elution with a solution of ammonia (0.88) in methanol gave the title compound as a white solid (89 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe product was dissolved in methanol
  4. washeluted through an SCX ion exchange cartridge
  5. washElution with a solution of ammonia (0.88) in methanol

Sources & evidence

ORD record
ord-132ca0880cab4604ae04c25033c0952d
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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