Hydrochloric Acid → HCID 57441097, compound

HRID 1987222Notes

Reaction equation

HRID 1987222 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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57723209HCID 57723209, compound

Product 1

HCID 57441097HCID 57441097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 1:1/2M HCl:EtOH 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 was washed with saturated aqueous NaCl solution and dried over anhydrous Na2SO4. The solvent was evaporated. Yield: 154 mg (92%). 1H NMR (400 MHz, METHANOL-D4) 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), 1.95-2.03 (m, 0.7 H), 2.05-2.11 (m, 2 H), 2.13-2.22 (m, 0.3 H), 4.37-4.44 (m, 2.7 H), 4.47-4.56 (m, 0.3 H), 7.11 (t, J=2.05 Hz, 0.5 H) 7.13 (t, J=2.05 Hz, 0.5 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 was washed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-51a3c4ea40bb418e9075131e8fad4aba
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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