Reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([NH:23]C(=O)C)=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>Cl.CCO>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 120 °C
Procedure
N-{2-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}acetamide (500 mg, 1.37 mmol) was dissolved in 10 mL of 2 M HCl-EtOH (1:1). The solution was divided into two sealed tubes (5 mL/tube). Each tube was heated at 120° C. in a Personal Chemistry microwaves instrument for 1 h. The fractions were pooled and the solvent was evaporated. The residue was diluted with 2 M NaOH and extracted (3×) with EtOAc. The organic phase was washed with saturated aqueous NaCl solution and dried over anhydrous Na2SO4. The solvent was evaporated. Yield: 440 mg (99%); 1H NMR (400 MHz, CDCl3) δ 1.40-1.52 (m, 2 H), 1.52-1.54 (m, 9 H), 1.56-1.66 (m, 4 H), 1.68-1.75 (m, 2 H), 2.07-2.17 (m, 3 H), 4.14 (d, J=7.62 Hz, 2 H), 6.65 (dd, J=8.50, 2.25 Hz, 1 H), 7.04-7.09 (m, 2 H).
Workup
- customthe solvent was evaporated
- additionThe residue was diluted with 2 M NaOH
- extractionextracted (3×) with EtOAc
- washThe organic phase was washed with saturated aqueous NaCl solution
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-b7684c6d45964afb842312730427c1cd
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615642B2
Linked notes
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