HCID 57438194, compound → HCID 67373666, compound

HRID 1375377Notes

Reaction equation

HRID 1375377 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][N:11]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=2)=[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:7]=[C:6]1[CH:39]=[CH2:40])[CH2:2][CH2:3][CH3:4]>C(OCC)(=O)C.[Pd]>[CH2:1]([N:5]1[C:9]([CH2:10][N:11]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]3[O:27][CH2:28][CH2:29][O:30][C:25]=3[CH:24]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=2)=[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:7]=[C:6]1[CH2:39][CH3:40])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 57438194HCID 57438194, compound

Product 1

HCID 67373666HCID 67373666, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-[(1-butyl-2-ethenyl-4-phenyl-1H-imidazol-5-yl)methyl]-N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-N-(3-ethoxybenzyl)-amine (8 mg) prepared in the previous example, is dissolved in 5 mL ethyl acetate and hydrogenated at room temperature under atmospheric pressure. 5% Pd/C (3 mg) is used as a catalyst. The reaction mixture is filtered through celite to provide the title compound (Compound 7). 1H NMR (CDCl3) δ 0.83(t, J=7.2 Hz, 3H), 1.10(m, 2H), 1.27(m, 2H), 1.31(t, J=7.2 Hz, 3H), 1.40(t, J=7.2 Hz, 3H), 2.66(q, 7.2 Hz, 2H) 3.30(s, 2H), 3.36(s, 2H), 3.65(s, 2H), 3.98(m, 4H), 4.23(s, 4H), 6.76(m, 4H), 7.17(t, J=7.6 Hz, 2H), 7.26(m, 1H), 7.37(t, J=7.6 Hz, 2H), 7.58(d, J=7.6 Hz, 2H).

Workup

  1. filtrationThe reaction mixture is filtered through celite

Sources & evidence

ORD record
ord-edf2afe4cd464897ac2e153004f72658
Source dataset
uspto-grants-2007_01
Patent number
US07169775B2

Reaction notes

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