1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 46831860, compound

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Reaction Steps

To a mixture of EXAMPLE 175E (66 mg), 3-nitro-4-((tetrahydro-2H-pyran-4-yl)methylamino)benzenesulfonamide (75 mg) and 4-dimethylaminopyridine (58.4 mg) in dichloromethane (5 mL) was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (45.8 mg). The mixture was stirred at ambient temperature overnight and concentrated. The concentrate was purified by RP HPLC (10-70% acetonitrile in 0.1% trifluoroacetic aicd water/70 minutes). The desired fractions were concentrated to remove acetonitrile and the concentrate was diluted with dichloromethane and neutralized with aqueous NaHCO3. The dichloromethane layer was dried over Na2SO4 and concentrated to provide the title compound. 1H NMR (500 MHz, dimethysulfoxide-d6) δ ppm 11.31 (1 H, s), 11.25 (1 H, s), 8.62 (1 H, t), 8.50 (1 H, d), 7.68 (1 H, dd), 7.53 (2 H, d), 7.46 (2 H, d), 7.37 (1 H, t), 7.24-7.31 (4 H, m), 7.17 (1 H, d), 7.12 (1 H, dd), 7.07 (1 H, d), 6.96(1 H, t), 6.69 (1 H, dd), 6.42 (1 H, d), 6.26 (2 H, s), 3.85 (2 H, dd), 3.21-3.33 (5 H, m), 3.01 (4 H, s), 2.29-2.39 (2 H, m), 2.15-2.22 (2 H, m), 1.83-1.94 (1 H, m), 1.57-1.68 (2 H, m), 1.22-1.31 (2 H, m), 1.17 (3 H, d).

Provenance & Evidence