Trifluoroacetic acid → HCID 89443037, compound

HRID 2284049Notes

Reaction equation

HRID 2284049 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:18]([CH2:33][CH:34]3C[CH2:37][CH2:36][N:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=3)N=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.FC(F)(F)C(O)=O.C([O-])=O.[NH4+:56]>CO.[Pd]>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[N:56]=[C:17]([CH:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)[N:18]([CH:33]3[CH2:37][CH2:36][N:35]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:34]3)[CH:19]=2)=[CH:23][C:24]=1[C:29]([F:30])([F:32])[F:31]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2723923Ammonium formateHCID 89442782HCID 89442782, compound

Product 1

HCID 89443037HCID 89443037, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[1-(1-tert-butoxycarbonyl-pyrrolidin-2-ylmethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (200.00 mg; 0.32 mmol; 1.00 eq.) in methanol 5 ml added trifluoro-acetic acid (54.24 mg; 0.48 mmol; 1.50 eq.), stirred at RT for 5 min, added ammonium formate (199.96 mg; 3.17 mmol; 10.00 eq.) and 200 mg wet 10% Pd/C, stirred at RT for 1 hr, lc-ms showed clean desired. Removed off solvent, added EA 50 ml, washed with Brine and 5% NaHCO3, dried, removed off solvent, got title compound 110 mg, yield 70%.

Workup

  1. stirringstirred at RT for 1 hr
  2. customRemoved off solvent
  3. additionadded EA 50 ml
  4. washwashed with Brine and 5% NaHCO3
  5. customdried
  6. customremoved off solvent

Sources & evidence

ORD record
ord-30b03763aab4466da500cc5fe9643d9e
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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