Dimethylformamide → HCID 136348819, compound

Participants

Reaction Steps

A solution of PyBOP (38 mg, 70 umol) in DMF (0.1 ml) was added to a mixture of 4-({3-(3,5-dichlorophenyl)-5-[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-1-yl}methyl)benzoic acid (20 mg, 36 umol), tert-butyl β-alanine hydrochloride (27 mg, 4 eq.), DIEA (40 ul, 6 eq.) in DMF (0.3 ml). The reaction was quenched with CH3CN:water (5% TFA) and purified with reverse phase HPLC to give tert-butyl N-[4-({3-(3,5-dichlorophenyl)-5-[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-1-yl}methyl)benzoyl]-β-alaninate as an oil residue. This was treated with TFA/DCM (1:2) and the product was lyophilized to give N-[4-({3-(3,5-Dichlorophenyl)-5-[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-1-yl}methyl)benzoyl]-β-alanine as a white powder. NMR (500 MHz, DMSO-d6) δ: 2.43 (t, 2H); 3.4 (q, 2H); 6.18 (s, 2H); 7.26 (br d, J=9.2 Hz, 1H); 7.38 (d, J=8.5 Hz, 2H); 7.59 (s, 1H); 7.61 (t, J=1.9 Hz, 1H); 7.67 (br s, 1H); 7.72 (d, J=8.5 Hz, 2H); 7.74 (br d, J=9.2 Hz, 1H); 7.82 (d, J=1.9 Hz, 2H). MS Cald for C28H20Cl2F3N5O4: 617.08; Obsd (M+1): 618.21.

Provenance & Evidence