(4-chlorophenyl)-phenylmethanamine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 2-chlorobenzimidazole and 4-chlorobenzhydrylamine HCl by Procedure A. The product was isolated by preparative LCMS to give the title compound as the free base (white solid, mp 180-184° C.). MS(ES+)m/z 334 ([M+1]+, 100). 1NMR (DMSO-d6) δ 6.18 (d, 1H), 6.80-6.90 (m, 2H), 7.08-7.14 (m, 2H), 7.20-7.40 (m, 9H), 7.66 (d, 1 H), 10.6 (s, 1 H). The product was isolated by preparative LCMS

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 2-chlorobenzimidazole and 4-chlorobenzhydrylamine HCl by Procedure A. The product was isolated by preparative LCMS to give the title compound as the free base (white solid, mp 180-184° C.). MS(ES+)m/z 334 ([M+1]+, 100). 1NMR (DMSO-d6) δ 6.18 (d, 1H), 6.80-6.90 (m, 2H), 7.08-7.14 (m, 2H), 7.20-7.40 (m, 9H), 7.66 (d, 1 H), 10.6 (s, 1 H). The product was isolated by preparative LCMS

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 7.9 mmol C-(4-chloro-phenyl)-C-phenyl-methylamine hydrochloride (CA [5267-39-0]) in 100 ml acetonitrile was treated successively with 7.9 mmol N-tert.butyloxycarbonyl glycine, 39 mmol DIPEA and 8.7 mmol TBTU. After stirring for 1 hour at room temperature, the mixture was concentrated. Chromatography (SiO2; ethyl acetate/cyclohexane) yielded the title compound as a colorless solid. Yield=84%. the mixture was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and [3-(4-methoxy-phenyl)-propionylamino]-acetic acid (Example 2.2).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and [3-(4-methoxy-phenyl)-propionylamino]-acetic acid (Example 2.2).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and [3-(4-chloro-phenyl)-propionylamino]-acetic acid (Example 2.1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and phenylacetylamino-acetic acid (CA [500-98-1]).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and benzyloxycarbonylamino-acetic acid (CA [1138-80-3]).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and benzyloxycarbonylamino-acetic acid (CA [1138-80-3]).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and hippuric acid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from rac-4-chlorobenzhydrylamine hydrochloride and benzyloxycarbonylamino-acetic acid (CA [1138-80-3]).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-(4,4,4-trifluoro-3-oxo-1-butyl)phenoxyacetic acid (0.374 g, 1.35 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.17 ml, 2.03 mmol) and a trace of N,N-dimethylformamide. After 30 min at 22° C., the solvent and excess reagent were evaporated under reduced pressure and the residual oil obtained was dissolved in anhydrous tetrahydrofuran (10 ml). This solution was then added dropwise to a vigorously stirred solution of p-chlorobenzhydrylamine hydrochloride (0.39 g, 1.35 mmol) in a mixture of tetrahydrofuran (10 ml) and 40% aqueous sodium acetate (10 ml). After 30 min at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried. Evaporation of the solvent under reduced pressure gave a solid which was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (8:2) gave 0.603 g (87%) of the title product as white crystals: mp 145-146° C. the solvent and excess reagent were evaporated under reduced pressure the residual oil obtained After 30 min at 22° C. washed with water, brine dried Evaporation of the solvent under reduced pressure gave a solid which was chromatographed on silica gel Elution with a mixture of toluene and ethyl acetate (8:2)