HCID 57723209, compound → HCID 57441097, compound

HRID 1435532Notes

Reaction equation

HRID 1435532 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][CH:14]([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:18]=[CH:19][C:20]([NH:22]C(=O)C)=[CH:21][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[CH2:12][CH2:13][CH:14]([F:17])[CH2:15][CH2:16]2)[C:8]2[CH:18]=[CH:19][C:20]([NH2:22])=[CH:21][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 57723209HCID 57723209, compound

Product 1

HCID 57441097HCID 57441097, compound

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

N-{2-tert-Butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}acetamide (190 mg, 0.550 mmol) was heated in 5 mL of 2 M HCl/EtOH (1:1) at 120° C. for 1 h using a Personal Chemistry microwaves apparatus. The solvent was evaporated. The residue was basified with 2M NaOH and extracted (3×) with EtOAc. The organic phase washed with saturated aqueous NaCl solution and dried over anhydrous Na2SO4. The solvent was evaporated. Yield: 154 mg (92%). 1H NMR (400 MHz, CD3OD) δ 1.28-1.39 (m, 2 H), 1.41-1.50 (m, 1 H), 1.53-1.59 (m, 1 H), 1.61-1.64 (m, 9 H), 1.69 (d, J=7.81 Hz, 2 H), 1.95-2.22 (m, 3 H), 4.37-4.83 (m, 3 H), 7.11-7.13 (m, 1 H), 7.15-7.18 (m, 1 H), 7.67-7.73 (m, 1 H).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted (3×) with EtOAc
  3. washThe organic phase washed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2f54c563b85841c7a08b06018518a834
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…