4-(Benzyloxy)-N-[5-cyano-2-(cyclohexylamino)phenyl]benzamide → 2-[4-(Benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

HRID 392963Notes

Reaction equation

HRID 392963 reaction equation
[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:12]([C:13]([NH:15][C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=2[NH:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:12]([C:13]2[N:24]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:17]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 226608044-(Benzyloxy)-N-[5-cyano-2-(cyclohexylamino)phenyl]benzamide

Product 1

HCID 226607902-[4-(Benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrileYield 90.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of compound 11 (2.08 g, 4.89 mmol) in acetic acid (15 mL) was refluxed for 4.5 h. The reaction mixture was cooled to rt and concentrated on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3 (2×) and water (1×). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator. The residue was recrystallized from hexane/ethyl acetate to give compound 12 as a tan solid (1.8 g, 90%). ESI-MS m/e 408.3 (M+1).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3 (2×) and water (1×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-9fb2d8b3721448078a628c2c7bec5314
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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