4-Methylmorpholine → HCID 70095140, compound

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).

1. waitwas then left
2. customSolvent was evaporated
3. extractionextracted with ETOAC (3×70 ml)
4. washwashed with a saturated solution of NaHCO3
5. dry with materialdried over MgSO4
6. customevaporated
7. customThe crude residue was then purified by flash column chromatography

ORD record

ord-74e53e08efe346fab736d44edcc3e2d0

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960594B2