Ammonium formate → HCID 86608218, compound

HRID 1593683Notes

Reaction equation

HRID 1593683 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([NH:18][C:19]([CH:21]3[CH2:26][CH2:25][N:24](CC4C=CC=CC=4)[CH2:23][CH2:22]3)=[O:20])=[N:16][NH:15][C:12]2=[N:13][N:14]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([NH:18][C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[O:20])=[N:16][NH:15][C:12]2=[N:13][N:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86608219HCID 86608219, compound

Product 1

HCID 86608218HCID 86608218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-piperidine-4-carboxylic acid [5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridazin-3-yl]-amide (Example 209; 340 mg, 0.76 mmol), ammonium formate (191 mg, 3.03 mmol) and 10% Pd/C (50 mg) in ethanol (10 mL) was stirred at reflux for 72 h. The reaction mixture was cooled, filtered through celite and concentrated. The residue was purified by chromatography on silica gel using initially 10% v/v methanol in dichloromethane and rising to 10% v/v 2N methanolic ammonia in dichloromethane to afford the title compound, a powder.

Workup

  1. temperatureat reflux for 72 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel using initially 10% v/v methanol in dichloromethane

Sources & evidence

ORD record
ord-ed6f63885d0842219885bfe2780578ff
Source dataset
uspto-grants-2007_11
Patent number
US07297792B2

Reaction notes

Loading…