5-((2-phenoxybenzyloxy)methyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole → HCID 178420502, compound

HRID 397821Notes

Reaction equation

HRID 397821 reaction equation
[O:1]([C:8]1[CH:44]=[CH:43][CH:42]=[CH:41][C:9]=1[CH2:10][O:11][CH2:12][CH:13]1[CH2:40][CH2:39][C:16]2[N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=[N:19][C:15]=2[CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C1C=CC=CC=1COCC1CCC2N=CN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=2C1)C1C=CC=CC=1>C(O)(=O)C.O>[O:1]([C:8]1[CH:44]=[CH:43][CH:42]=[CH:41][C:9]=1[CH2:10][O:11][CH2:12][CH:13]1[CH2:40][CH2:39][C:16]2[NH:17][CH:18]=[N:19][C:15]=2[CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 230012175-((2-phenoxybenzyloxy)methyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazoleHCID 230012495-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole

Product 1

HCID 178420502HCID 178420502, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-((2-phenoxybenzyloxy)methyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole (1.20 g, 2.1 mmol) was dissolved in a mixture of acetic acid (9 ml) and water (1 ml). The mixture was heated to 90° C. for 2 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (10 ml). a 3.5 M solution of hydrogen chloride in ethyl acetate (0.60 ml) was added. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using DCM/methanol/25% aqueous ammonia (first: 100:10:1, then 100:20:2) as eluent to give 74 mg of the title compound. For biological testing, the title compound was transferred into its hydrochloride salt by lyophilization of its solution in 0.1 N hydrochloric acid (40 ml).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
  3. additiona 3.5 M solution of hydrogen chloride in ethyl acetate (0.60 ml) was added
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (40 g)

Sources & evidence

ORD record
ord-2338b4d229ce403583c58419d2206453
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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