HCID 10222542, compound → HCID 9969044, compound

HRID 238488Notes

Reaction equation

HRID 238488 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 C21H21PN4O—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-8f7d076d386e4343a051357f59b53be9
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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