HCID 11612403, compound → HCID 11518384, compound

HRID 1790174Notes

Reaction equation

HRID 1790174 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][N:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:23]=[CH:22]4)[C:15]2=[O:35])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CC(O)=O.[Pd]>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:23]=[CH:22]4)[C:15]2=[O:35])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11612403HCID 11612403, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11518384HCID 11518384, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-(4-phenoxyphenyl)-3-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-yl]-1,3-dihydro-2H-imidazol-2-one (Example 118) (0.100 g, 0.215 mmol) was dissolved in 20 mL of AcOH and 100 mg of Pd/C (10% mol/mol) was added. The mixture was subjected to an atmosphere of hydrogen gas at a pressure of 60 psi in a Parr shaker apparatus, and shaken at room temperature for 6 hours. The mixture was filtered through celite, and the solvents removed under reduced pressure. The residue was purified by RP-HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.52–1.77 (m, 4 H) 2.34–2.50 (m, 4 H) 2.87 (t, J=6.61 Hz, 2 H) 3.88–4.13 (m, 4 H) 4.50 (t, J=6.61 Hz, 2 H) 6.93–7.02 (m, J=7.80 Hz, 2 H) 7.03–7.15 (m, 3 H) 7.33–7.45 (m, J=8.65, 7.29 Hz, 2 H) 7.61–7.72 (m, 3 H) 7.72–7.78 (m, J=2.03 Hz, 1 H) 7.79–7.89 (m, 1 H) 8.02 (s, 1 H); MS (ESI) m/z 468 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvents removed under reduced pressure
  3. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-84c8be1d487f4a98ba71233dc7b69f16
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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