Triethylamine → HCID 68313780, compound

Participants

Reaction Steps

To a solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (200 mg, 0.71 mmol) and Et3N (0.20 mL, 1.42 mmol) in dry THF was added phenyl carbonochloridate (98 μL, 0.78 mmol) and the reaction mixture maintained at RT for 1 hr. An aliquot of (R)—N,N-dimethylpyrrolidin-3-amine (270 μL, 2.13 mmol) was added to this mixture and after 15 hr at RT a second aliquot of (R)—N,N-dimethylpyrrolidin-3-amine (100 μL, 0.79 mmol) was added and the mixture was maintained at RT for a further 1 hr. The resulting mixture was partitioned between aq. NH4Cl (10 mL) and DCM (10 mL) and the aqueous layer was separated and extracted with DCM (3×10 mL) The combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, [5% MeOH in DCM] in DCM, 0-100%, gradient elution and then, 10% [2% NH3 (7M in MeOH) in MeOH] in DCM, isocratic elution and finally, 30% MeOH in DCM, isocratic elution) to afford (R)-3-(dimethylamino)-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)pyrrolidine-1-carboxamide, Intermediate K1, as a yellow/brown solid (250 mg, 81%); Rt 1.54 min (Method 2); m/z 422 (M+H)+ (ES+).

Provenance & Evidence