HCID 178418361, compound → HCID 178509631, compound

HRID 1797001Notes

Reaction equation

HRID 1797001 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[NH:19][CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[N:22]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.[H][H]>[Pd].[C]>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([C:21]2[N:22]=[C:18]([CH:15]3[CH2:14][CH2:13][CH:12]([CH2:11][NH2:10])[CH2:17][CH2:16]3)[NH:19][CH:20]=2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178522787HCID 178522787, compound

Product 1

HCID 178509631HCID 178509631, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

An ethanolic solution of {4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-carbamic acid benzyl ester (4.15 g, 0.0091 mol) and 10% Pd/Carbon (400 mg) was shaken overnight under 55 psi of hydrogen in a Paar apparatus. The mixture was filtered through celite and concentrated under reduced pressure to give a foam, which was triturated with EtOAc/Hexanes/MeOH to produce C-{4-[4-(3-trifluoromethyl-phenyl)-1H-imidazole-2-yl]-cyclohexyl}-methylamine as a filterable solid. 1H NMR (DMSO-d6): δ 0.93–1.05 (m, 2H), 1.30–1.4 (m, 2H), 1.42–1.55 (m, 2H), 1.85 (d, J=12.8 Hz, 2H), 1.99 (d, J=11.6 Hz, 2H), 2.4–2.5 (m, 1H), 2.56–2.66 (m, 1H), 7.43–7.48 (m, 1H), 7.50–7.55 (m, 1H), 7.63 (s, 1H), 7.99 (d, J=7.9 Hz, 1H), 8.02 (s, 1H). MS 324 (M+H)+

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customto give a foam, which
  4. customwas triturated with EtOAc/Hexanes/MeOH

Sources & evidence

ORD record
ord-83d1f0e41d0a486f9f7b84b61b806266
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

Loading…