HCID 178522225, compound → HCID 178522224, compound

HRID 1630296Notes

Reaction equation

HRID 1630296 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([N:9]2[CH2:14][CH2:13][N:12](C(OCC3C=CC=CC=3)=O)[CH2:11][C@H:10]2[C:25](=[O:41])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)=[O:8])[N:3]=[CH:2]1>[Pd].CO>[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[C:25]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:31][CH:32]=2)=[O:41])=[O:8])[N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 178522225HCID 178522225, compound

Product 1

HCID 178522224HCID 178522224, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step (a) A flask was charged with (S)-benzyl 4-(2-(1H-imidazol-4-yl)acetyl)-3-(4-(4-fluorophenoxy)phenylcarbamoyl)piperazine-1-carboxylate (0.80 g, 1.4 mmol), prepared as in Example 13, methanol (10 mL) and palladium on carbon (10%, 100 mg) and the mixture was stirred at ambient temperature. The reaction mixture was placed under a hydrogen atmosphere (balloon) for 14 hours and then exposed to air, filtered through celite and concentrated. Product was purified from residue by reverse phase HPLC to give (S)-1-(2-(1H-imidazol-4-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (0.5 g, 83% yield) as an off-white solid. 1H-NMR (400 MHz, CDCl3): 10.02 (s, 1H), 9.20 (s, 1H), 7.63-7.56 (m, 2H), 7.52 (s, 1H), 7.05-6.93 (m, 7H), 5.34 (s, 1H), 4.05-4.00 (m, 1H), 3.94-3.86 (m, 1H), 3.78-3.71 (m, 2H), 3.28-3.20 (m, 1H), 3.00-2.94 (m, 1H), 2.89-2.74 (m, 2H), 2.61-2.53 (m, 1H). MS (EI) for C22H22FN5O3. found 424.2 (MH+).

Workup

  1. customfor 14 hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated
  4. customProduct was purified from residue by reverse phase HPLC

Sources & evidence

ORD record
ord-8ba1d27becc94b70a3d5d67f18418561
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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