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

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).

1. concentrationconcentrated
2. customThe concentrate was purified by RP HPLC (10-70% acetonitrile in 0.1% trifluoroacetic aicd water/70 minutes)
3. concentrationThe desired fractions were concentrated
4. customto remove acetonitrile
5. additionthe concentrate was diluted with dichloromethane and neutralized with aqueous NaHCO3
6. dry with materialThe dichloromethane layer was dried over Na2SO4
7. concentrationconcentrated

ORD-Eintrag

ord-36e9cc9b7f414b33bc21ad75a6b4d5d9

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08563735B2