Pyridine → HCID 42635494, compound

Participants

Reaction Steps

[3,5-Bis(trifluoromethyl)benzyl]-((3S,5R)-5-ethyl-pyrrolidin-3-yl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine (84 mg, 0.17 mmol) and triphosgene (71 mg, 0.24 mmol) are dissolved in CH2Cl2 (2 mL). The reaction mixture is stirred at room temperature for 1 hour after addition of pyridine (15 mg, 0.19 mmol). Saturated aqueous NH4Cl and EtOAc are added, then extracted with EtOAc. The combined organic layer is dried over Na2SO4 then concentrated under reduced pressure. The resulting residue is dissolved in CH2Cl2 (1.5 mL) and then pyrrolidine (60 mg, 0.85 mmol) is added. The reaction mixture is stirred at room temperature for 12 hours. Saturated aqueous NH4Cl and CH2Cl2 are added, then extracted with CH2Cl2. The combined organic layer is dried over MgSO4, then concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: n-hexane/EtOAc) to give ((2R,4S)-4-{(3,5-Bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-pyrrolidin-1-yl-methanone (45 mg, 36%); ESI-MS m/z: 596 [M+1]+, Retention time 4.52 min (condition B).

Provenance & Evidence