Diisopropylethylamine → HCID 66920833, compound

Participants

Reaction Steps

In a 20 mL vial a solution of Example 104A (32.5 mg, 0.16 mmol) dissolved in N,N-dimethylacetamide (0.8 mL) was added, followed by the addition of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (50.4 mg, 0.16 mmol) dissolved in N,N-dimethylacetamide (0.8 mL). Then, commercially available [5-(2-pyridinyl)-2-thienyl]methylamine (36.2 mg, 0.19 mmol) dissolved in N,N-dimethylacetamide (0.6 mL) was added followed by the addition of diisopropyl ethyl amine (57.9 uL, 0.31 mmol) dissolved in N,N-dimethylacetamide (0.8 mL). The mixture was shaken at room temperature overnight. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to give the titled compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.08-1.28 (m, 3H) 1.29-1.37 (m, 2H) 4.25-4.53 (m, 2H) 4.54-4.69 (m, 2H) 6.95-7.06 (m, 1H) 7.09-7.12 (m, 1H) 7.16-7.32 (m, 1H) 7.49-7.64 (m, 1H) 7.68-7.91 (m, 2H) 8.31-8.52 (m, 1H); MS (ESI) positive ion 380 (M+H).

Provenance & Evidence