4-Methylmorpholine → HCID 70095140, compound

Participants

Reaction Steps

Now referring to Scheme K, to Compound XXIII: thiophene-2,5-dicarboxylic acid monomethyl ester (923 mg, 4.96 mmol) in DMF (10 ml) was added 1-hydroxybenzotriazole (HOBT) (870 mg, 6.45 mmol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrocloride (EDC) (1.23 g, 6.45 mmol) and (1.2 ml, 10.9 mmol) of NMM. Compound XXIV: N,N′-Bis-(Boc)-N″-(2-Amino-ethyl)-guanidine (6.45 mmol, 1.96 g) was then added in DMF(10 ml) to the reaction mixture which was then left to stir at room temperature for 16 hours. Solvent was evaporated and the residue was thrown in a 10% citric acid solution (50 ml) and extracted with ETOAC (3×70 ml). The organic phases were combined and washed with a saturated solution of NaHCO3 followed by a solution of Brine, dried over MgSO4 and evaporated. The crude residue was then purified by flash column chromatography using CH2Cl2/MeOH (10:0.2) to give the desired product (Compound XXVII) in 94% yield. 1H NMR (CDCl3, 400 MHz) δ 1.1-1.34 (m, 21H), 3.41-3.81 (m, 4H), 3.88 (s, 3H), 5.58-5.59 (d, 1H), 7.69-7.70 (d, 1H), 8.43-8.54 (broad s, 1H), 8.70-8.88 (m, 1H).

Provenance & Evidence