7-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one → 1-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dione

HRID 913057Notes

Reaction equation

HRID 913057 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[N:19]=2)=[O:14])OCC[O:3]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[C:18]1[NH:19][C:15]([C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:2](=[O:3])[CH3:1])=[N:16][CH:17]=1

Participants

3

Reactant 1

HCID 673819037-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one

Product 1

HCID 673820661-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dione

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The ketone E3 was dissolved in TFA/DCM (1:1) and stirred for 4 hr at RT. After evaporation of the solvent under reduced pressure, the crude product was purified by preparative RP-HPLC (column: C18), using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents. The desired fractions were lyophilized to afford E4 as a white solid. 1H NMR (300 MHz, DMSO) δ: 8.17 (1H, s), 7.92-7.79 (3H, m), 7.76-7.64 (2H, m), 7.55-7.45 (2H, m), 3.15 (2H, t, J=7.4 Hz), 2.44 (2H, t, J=7.4 Hz), 2.15 (3H, s), 1.74 (2H, m), 1.58 (2H, m), 1.37 (4H, m). MS (ES) C22H24N2O2 requires: 348, found: 349 (M+H)+.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe crude product was purified by preparative RP-HPLC (column: C18)

Sources & evidence

ORD record
ord-9355b57f29894febab783def4cdc4217
Source dataset
uspto-grants-2011_09
Patent number
US08026265B2

Reaction notes

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