((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride → [1-(4-Bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1h-pyrazol-4-yl]-[4-((s)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

Participants

Reaction Steps

In analogy to the procedure described in Example 160E], a mixture of 5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid and 1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazole-4-carboxylic acid (example 173D]) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanoldihydrochloride (Example 161A]) gave a mixture of the title compound and example 175. Purification by reversed phase HPLC (MeCN:H2O) afforded [4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-methanone (Example 175) and [1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone) as a white solid (31%). MS: 593.4 (1 Br, MH+).

Provenance & Evidence