N-(3-Aminopropyl)morpholine → HCID 2848698, compound

Participants

Reaction Conditions

Reaction Steps

2-chloro-5-nitro-pyridine Compound 16a1 (6.06 g, 38.2 mmol) and 3-morpholin-4-yl-propylamine Compound 9a (6.27 mL, 42.1 mmol) were combined in DMSO (100 mL) and heated to 50° C. After 2.5 hours the reaction mixture was diluted with 0.5 M HCl and washed with ethyl ether. The aqueous layer was adjusted to pH 11 with NaOH and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to provide (3-morpholin-4-yl-propyl)-(5-nitro-pyridin-2-yl)-amine Compound 19a1. Using the procedure of Example 1, Compound 19a1 was used in place of Compound 1n3 with AcOH (30 mL) replacing EtOAc as solvent. 10% Pd/C (3.1 g) was added to the solution and the reaction was carried forward to provide N2-(3-morpholin-4-yl-propyl)-pyridine-2,5-diamine Compound 19a. 1H NMR (CDCl3) δ 7.67 (d, J=3.0 Hz, 1H); 6.95 (dd, J=8.6, 3.0 Hz, 1H); 6.31(d, J=8.6 Hz, 1H); 3.77-3.66 (m, 4H); 2.52-2.38 (m, 8H); 2.08.(p, J=6.8Hz, 2H). MS 267 (MH+).

Provenance & Evidence