HCID 23001243, compound → HCID 178506163, compound

HRID 397831Notes

Reaction equation

HRID 397831 reaction equation
[Cl:1][C:2]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[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(C(F)(F)F)=CC=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[C:38]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:36]=[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 23001243HCID 23001243, compoundHCID 23001258HCID 23001258, compound

Product 1

HCID 178506163HCID 178506163, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of a mixture of 5-(2-chloro-3-(trifluoromethyl)benzyloxymethyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-(2-chloro-3-(trifluoromethyl)benzyloxymethyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole in a mixture of acetic acid (9 ml) and water (1 ml) was heated to 70° C. for 2 hour. 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 25 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-31584df5ab90437d8c73cec08ad1e99b
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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