Ammonium formate → HCID 89464462, compound

HRID 881978Notes

Reaction equation

HRID 881978 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[N:17]=[C:16]([N:18]4[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:26](=[O:43])[C:27]5[CH:32]=[C:31]([O:33]C)[CH:30]=[C:29]([O:35][CH2:36]C6C=CC=CC=6)[CH:28]=5)[CH2:20][CH2:19]4)[CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])=O.[NH4+]>[Pd].CO>[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[N:17]=[C:16]([N:18]4[CH2:19][CH2:20][CH:21]([CH2:24][NH:25][C:26](=[O:43])[C:27]5[CH:28]=[C:29]([O:35][CH3:36])[CH:30]=[C:31]([OH:33])[CH:32]=5)[CH2:22][CH2:23]4)[CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89471763HCID 89471763, compound

Product 1

HCID 89464462HCID 89464462, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-((1-(2-(3-(1H-pyrazol-1-yl)phenyl)pyrimidin-4-yl)piperidin-4-yl)methyl)-3-(benzoxy)-5-methoxybenzamide (Example 11, step iv, 1.45 g, 2.5 mmol), ammonium formate (0.70 g, 11.1 mmol) and 10% palladium on carbon (0.15 g) in methanol (30 ml) was heated to reflux temperature for 18 hours. The reaction mixture was cooled to ambient temperature and filtered through celite. The filtrate was concentrated under reduced pressure and the residue obtained was partitioned between CH2Cl2 and water. The organic phase was passed through a hydrophobic frit and concentrated under reduced pressure to give N-((1-(2-(3-(1H-pyrazol-1-yl)phenyl)pyrimidin-4-yl)piperidin-4-yl)methyl)-3-hydroxy-5-methoxybenzamide as a pale yellow foam (1.16 g). MS (ESI) me: 485.6 (M+H)+.

Workup

  1. temperatureto reflux temperature for 18 hours
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue obtained
  5. customwas partitioned between CH2Cl2 and water
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb0a5ec4c9a94eba9cd90f3dc58e52ff
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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