Ammonium formate → HCID 71515634, compound

HRID 574200Notes

Reaction equation

HRID 574200 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]([C:22]1[O:26][C:25]([C:27]2[C:32]([NH2:33])=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[C:29]([O:38][CH3:39])[N:28]=2)=[N:24][N:23]=1)([CH3:21])[C:17]([F:20])([F:19])[F:18])C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[OH-].[OH-].[Pd+2]>[NH2:33][C:32]1[C:27]([C:25]2[O:26][C:22]([C:16]([OH:15])([CH3:21])[C:17]([F:20])([F:19])[F:18])=[N:23][N:24]=2)=[N:28][C:29]([O:38][CH3:39])=[C:30]([C:34]([F:35])([F:37])[F:36])[CH:31]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86729589HCID 86729589, compound

Product 1

HCID 71515634HCID 71515634, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of 2-(5-(2-(benzyloxy)-1,1,1-trifluoropropan-2-yl)-1,3,4-oxadiazol-2-yl)-6-methoxy-5-(trifluoromethyl)pyridin-3-amine trifluoroacetate (Step 3) (450 mg, 0.973 mmol) in EtOH (25 ml) was added palladium hydroxide on carbon (45.1 mg, 0.321 mmol) followed by ammonium formate (614 mg, 9.73 mmol). The mixture was heated at reflux for 1 h and then filtered through Celite® washing through with EtOH followed by water. The ethanol was removed in vacuo and the resultant aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the title product; 1H NMR (400 MHz, DMSO-d6) δ 7.85 (1H, s), 7.74 (1H, s), 6.74 (2H, s), 3.94 (3H, s), 1.86 (3H, s). LC-MS Rt=1.17 min [M+H]+ 373.1 Method: 2minLC_v003.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationfiltered through Celite®
  4. washwashing through with EtOH
  5. customThe ethanol was removed in vacuo
  6. extractionthe resultant aqueous phase was extracted with EtOAc
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f7657a39a354e6d93c7608a89006902
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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