HCID 23001237, compound → HCID 178506171, compound

HRID 397826Notes

Reaction equation

HRID 397826 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:3]=1[CH2:4][O:5][CH2:6][CH:7]1[CH2:34][CH2:33][C:10]2[N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:12]=[N:13][C:9]=2[CH2:8]1.ClC1C=CC(C(F)(F)F)=CC=1COCC1CCC2N=CN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=2C1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:38]=[CH:37][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:35][C:3]=1[CH2:4][O:5][CH2:6][CH:7]1[CH2:34][CH2:33][C:10]2[NH:11][CH:12]=[N:13][C:9]=2[CH2:8]1

Participants

5

Reactant 2

HCID 23001237HCID 23001237, compoundHCID 23001247HCID 23001247, compound

Product 1

HCID 178506171HCID 178506171, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of a mixture of 5-(2-chloro-5-trifluoromethylbenzyloxymethyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-(2-chloro-5-trifluoromethylbenzyloxymethyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole in a mixture of acetic acid (5 ml) and water (0.6 ml) was heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using a mixture of DCM/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 310 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silica (40 g)
  4. additiona mixture of DCM/methanol/25% aqueous ammonia (100:10:1) as eluent

Sources & evidence

ORD record
ord-28a83b5018f043afa1d6e9ae8e94b90a
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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