1,3-Dihydro-1-(4-phenoxyphenyl)-3-[2-[2-(1-pyrrolidinyl)ethyl]-2H-indazol-5-yl]-2H-imidazol-2-one → HCID 11431273, compound

HRID 1825843Notes

Reaction equation

HRID 1825843 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:27]=[CH:26][C:25]4[C:21](=[CH:22][N:23]([CH2:28][CH2:29][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:24]=4)[CH:20]=3)[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:27]=[CH:26][C:25]4[C:21](=[CH:22][N:23]([CH2:28][CH2:29][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:24]=4)[CH:20]=3)[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 113287901,3-Dihydro-1-(4-phenoxyphenyl)-3-[2-[2-(1-pyrrolidinyl)ethyl]-2H-indazol-5-yl]-2H-imidazol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 11431273HCID 11431273, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-(4-phenoxyphenyl)-3-[2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-yl]-1,3-dihydro-2H-imidazol-2-one (Example 84) (0.100 g, 0.215 mmol) was taken up in 20 mL of AcOH along with 100 mg of Pd/C (10% mol/mol) and the mixture was subjected to an atmosphere of hydrogen gas at a pressure of 60 psi in a Parr shaker apparatus. The mixture was shaken at room temperature for 6 hours after which the mixture was filtered through a bed of celite, and the solvents removed under reduced pressure. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.75–2.06 (m, 4 H) 3.02–3.15 (m, 2 H) 3.47–3.63 (m, 2 H) 3.74–3.87 (m, 2 H) 3.93–4.12 (m, 4 H) 4.82 (t, J=5.76 Hz, 2 H) 6.94–7.01 (m, 2 H) 7.03–7.14 (m, 3 H) 7.34–7.34 (m, 2 H) 7.62–7.70 (m, 4 H) 7.86 (dd, J=9.49, 2.03 Hz, 1 H) 8.39–8.46 (m, 1 H); MS (ESI) m/z 468 [M+H]+.

Workup

  1. filtrationwas filtered through a bed of celite
  2. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-abd504994700461fbbecf21f72188881
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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