Ammonium formate → HCID 59559658, compound

HRID 1178005Notes

Reaction equation

HRID 1178005 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:43]=[CH:42][C:16]([C:17]([NH:19][CH:20]([CH3:41])[C:21](=[O:40])[N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]([F:38])([F:37])[F:36])[CH2:24][CH2:23]2)=[O:18])=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH:20]([CH3:41])[C:21](=[O:40])[N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]([F:38])([F:37])[F:36])[CH2:24][CH2:23]2)=[O:18])=[CH:42][CH:43]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59559649HCID 59559649, compound

Product 1

HCID 59559658HCID 59559658, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (49 mg, 0.77 mmol) was added to a stirred solution of 4-benzyloxy-N-{1-methyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (42 mg, 0.07 mmol) in MeOH (10 mL). 10% Pd/c (10 mg) was then added and the resulting mixture stirred at room temperature under an inert atmosphere. The reaction mixture was then stirred at reflux temperature for 2 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated. The residue was dissolved in EtOAc, washed with water, followed by saturated brine solution. The organic layer was dried over sodium sulphate and concentrated in vacuo to afford 28 mg (82% yield) of 4-hydroxy-N-{1-methyl-2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 95%. 1H NMR (DMSO-d6): δ 7.76 (d, 1H), 7.60 (m, 4H), 7.36 (t, 1H), 7.26 (t, 1H), 6.8 (d, 2H), 5.2 (m, 1H), 4.2 (m, 1H), 3.9-3.4 (m, 8H), 1.4 (dd, 3H).

Workup

  1. stirringThe reaction mixture was then stirred
  2. temperatureat reflux temperature for 2 hrs
  3. filtrationThe mixture was filtered over a bed of celite
  4. washThe celite was washed with MeOH
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with water
  8. dry with materialThe organic layer was dried over sodium sulphate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c395ffa54d0a42449a71b130fe4f6291
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…