HCID 68065509, compound → HCID 66832619, compound

HRID 2044072Notes

Reaction equation

HRID 2044072 reaction equation
[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:21]=[C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][N:32](C(OCC5C=CC=CC=5)=O)[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[C:19]([C:45](=[O:47])[NH2:46])=[CH:18][CH:17]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CCO.[Pd]>[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:17]=[CH:18][C:19]([C:45]([NH2:46])=[O:47])=[C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]4)=[CH:27][CH:28]=3)[N:21]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 68065509HCID 68065509, compound

Product 1

HCID 66832619HCID 66832619, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (R)-benzyl 4-(4-(6-(3-benzamidopiperidin-1-yl)-3-carbamoylpyridin-2-ylamino)phenyl)piperazine-1-carboxylate (1.12 g, 1.767 mmol) in EtOAc (10 mL) and EtOH (10.00 mL) was added Pd/C (0.188 g, 0.177 mmol) under nitrogen. The resulting mixture was hydrogenated at 50 psi in a parr shaker overnight. The reaction mixture was filtered and the filtrate was concentrated to give 870 mg of (R)-6-(3-benzamidopiperidin-1-yl)-2-(4-(piperazin-1-yl)phenylamino)nicotinamide. LCMS: (M+H)+=500.14. 1H NMR (400 MHz, CDCl3-MIX) δ ppm 10.64 (1H, s), 7.51-7.59 (3H, m), 7.35-7.44 (3H, m), 7.28-7.34 (2H, m), 6.96 (1H, d, J=7.03 Hz), 6.75 (2H, d, J=9.23 Hz), 6.01 (1H, d, J=8.79 Hz), 4.10 (1H, br. s.), 3.75-3.83 (1H, m), 3.66-3.73 (1H, m), 3.58-3.66 (1H, m), 3.47-3.57 (1H, m), 3.15-3.20 (4H, m), 2.88-2.95 (4H, m), 1.82-1.96 (2H, m), 1.65-1.76 (1H, m), 1.54-1.65 (1H, m).

Workup

  1. customwas hydrogenated at 50 psi in a parr shaker overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3c386b448aec40aebee79a2aa435d316
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

Loading…