Ammonium formate → HCID 71059930, compound

HRID 405242Notes

Reaction equation

HRID 405242 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:24])=[CH2:23])=[CH:18][C:17]=3[C:25]3[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:32])=[N:29][CH:30]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=3[C:25]3[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:32])=[N:29][CH:30]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86674278HCID 86674278, compound

Product 1

HCID 71059930HCID 71059930, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(5-(2-(((4′-fluoro-[1,1′-biphenyl]-4-yl)amino)methyl)-5-(prop-1-en-2-yl)phenyl)picolinamido)propanoic acid (46 mg, 0.09 mmol), ammonium formate (57 mg, 0.91 mmol) and 10% Pd—C (10 mg, 0.01 mmol) in MeOH (5 mL) was refluxed. After 1 h, the resulting mixture was filtered through celite and washed with DCM-MeOH. The filtrate was concentrated and purified via column chromatography to yield the title compound.

Workup

  1. temperaturewas refluxed
  2. filtrationthe resulting mixture was filtered through celite
  3. washwashed with DCM-MeOH
  4. concentrationThe filtrate was concentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-e46afdfe2bf64c4293b82b6cffd7d3e6
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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