HCID 86729592, compound → HCID 71515636, compound

HRID 574205Notes

Reaction equation

HRID 574205 reaction equation
C([O:8][C:9]([C:15]1[O:19][C:18]([C:20]2[C:21]([NH2:34])=[N:22][C:23]([C:30]([F:33])([F:32])[F:31])=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=2)=[N:17][N:16]=1)([CH3:14])[C:10]([F:13])([F:12])[F:11])C1C=CC=CC=1>CCO.[Pd]>[NH2:34][C:21]1[C:20]([C:18]2[O:19][C:15]([C:9]([OH:8])([CH3:14])[C:10]([F:13])([F:12])[F:11])=[N:16][N:17]=2)=[N:25][C:24]([C:26]([F:27])([F:29])[F:28])=[C:23]([C:30]([F:33])([F:32])[F:31])[N:22]=1

Participants

4

Reactant 1

HCID 86729592HCID 86729592, compound

Product 1

HCID 71515636HCID 71515636, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(5-(2-(benzyloxy)-1,1,1-trifluoropropan-2-yl)-1,3,4-oxadiazol-2-yl)-5,6-bis(trifluoromethyl)pyrazin-2-amine (Step 2) (50 mg, 0.100 mmol) in EtOH (3 ml) under N2 was charged with Pd/C (1.061 mg, 9.97 μmol) and placed under a positive pressure of H2 (0.35 bar) at RT overnight. The reaction mixture was filtered through Celite® (Filter Material) and washed through with ethanol (30 ml), followed by DCM (10 ml). The filtrate was concentrated in vacuo and the resulting crude product was purified by UV directed LC-MS eluting with MeCN/Water/0.1% TFA. The clean fractions were poured into EtOAc (50 ml) and washed with saturated NaHCO3 (50 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound to give a pale orange solid. 1H NMR (400 MHz, DMSO-d6) δ 9.22 (1H, broad hump), 8.1 (1H, broad hump), 7.92 (1H, s), 1.4 (3H, s). 19F NMR (400 MHz, DMSO-d6) Peak 1 at −61 ppm, peak 2 at −64 ppm, peak 3 at −79.4 ppm.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (Filter Material)
  2. washwashed through with ethanol (30 ml)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting crude product was purified by UV
  5. washeluting with MeCN/Water/0.1% TFA
  6. additionThe clean fractions were poured into EtOAc (50 ml)
  7. washwashed with saturated NaHCO3 (50 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-176d67d486d6463d90c314c5a549c937
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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