HCID 10222542, compound → HCID 9969044, compound

HRID 557342Notes

Reaction equation

HRID 557342 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[O:17])=[CH:4][C:3]=1[F:28]>CCO.[Pd]>[F:28][C:3]1[CH:4]=[C:5]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[O:17])[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[N:7][CH:2]=1

Participants

4

Reactant 1

HCID 10222542HCID 10222542, compound

Product 1

HCID 9969044HCID 9969044, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

{6-Chloro-5-fluoro-2-[(4-pyridylmethyl)amino](3-pyridyl)}-N-[4-(methylethyl)phenyl]carboxamide (50 mg, 0.125 mmol, from Example 66) dissolved in EtOH (10 mL) with TEA (0.5 mL) and suspended with Pd/C (10%, 5 mg). The mixture was stirred at RT under a H2 balloon for 45 min. The mixture was filtered through a layer of Celite® and the filtrate was concentrated in vacuo. The residue was partitioned between CH2Cl2 and aq. NaHCO3 (sat.). The organic solution was dried over Na2SO4 and concentrated in vacuo to give the title compound. MS: 365 (M+1). Calc'd. for C21H21FN4O−364.42.

Workup

  1. filtrationThe mixture was filtered through a layer of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between CH2Cl2 and aq. NaHCO3 (sat.)
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bc949e3e12048ee80701fa2b5147956
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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