HCID 59852913, compound → HCID 11589321, compound

HRID 2374090Notes

Reaction equation

HRID 2374090 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19](=[O:35])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC4C=CC=CC=4)[CH:22]=3)=[O:17])=[CH:11][C:10]=2[F:36])[CH:5]=[CH:4][N:3]=1>CCOC(C)=O.CO.[Pd]>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19](=[O:35])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)=[O:17])=[CH:11][C:10]=2[F:36])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 59852913HCID 59852913, compound

Product 1

HCID 11589321HCID 11589321, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)-3-(2-(3-(benzyloxy)phenyl)acetyl)urea (150 mg, 0.31 mmol) in a mixture of 5 mL of EtOAc and 3 mL of MeOH was added 10% Pd/C (200 mg). The suspension was stirred under H2 atmosphere for 1 h. Filtration, followed by concentration, provided the title compound (77 mg, 63%). 1H NMR (DMSO-d6) δ 10.95 (s, 1H), 10.54 (s, 1H), 9.35 (s, 1H), 7.74 (d, 1H, J=6.0 Hz), 7.68 (dd, 1H, J=13.0, 2.0 Hz), 7.30 (dd, 1H, J=9.0, 1.1 Hz), 7.23 (t, 1H, J=9.0 Hz), 7.07 (t, 1H, J=8.0 Hz), 6.69 (s, 1H), 6.68 (d, 1H, J=7.0 Hz), 6.62 (dd, 1H, J=7.0, 2.0 Hz), 6.10 (dd, 1H, J=6.0, 2.0 Hz), 5.90 (s, 2H), 5.73 (d, 1H, J=2.0 Hz), 3.27 (s, 2H); MS(ESI+) m/z 397 (M+H)+.

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-db2a8b482ccf4f019c47122434e742cb
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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