Pyridine → HCID 172930687, compound

Participants

Reaction Steps

2-(2-Aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (13 mg, 0.065 mmol) in DMF (2 ml) was treated with methanesulphonyl chloride (5 μl, 0.064 mmol) and N,N-diisopropylethylamine (11 μl, 0.063 mmol) as described in Example 7 (a). This was then treated successively with a solution of the amine from Example 29 (e) (25 mg, 0.060 mmol) in DMF (2 ml) and pyridine (5 μl, 0.062 mmol). After work-up the product was purified by chromatography on silica gel eluting with 50, 70 and 100% ethyl acetate in hexane to yield the title compound (25 mg, 70%) as a yellow foam; νmax (CH2Cl2) 3389, 1784, 1722, 1690, 1607 and 1516 cm-1 ; δH (CDCl3, 250 MHz) 1.23 (3 H, s), 1.29 (3 H, s), 1.61-1.84 (3 H, m), 2.31 (1 H, m), 3.40 and 3.63 (2 H, ABq, J 18.7 Hz), 3.81 (3 H, s), 4.20 (3 H, s), 4.99 (1 H, d, J 4.8 Hz), 5.05 (1 H, dd, J 8.1, 8.1 Hz), 5.13 and 5.23 (2 H, ABq, J 11.8 Hz), 5.90 (1 H, dd, J 8.9, 4.8 Hz), 6.90 (2 H, d, J 8.7 Hz), 7.23 (1 H, s), 7.34 (2 H, d, J 8.7 Hz), 7.50 (2 H, br s, exch.) and 7.68 (1 H, br d, J 8.9 Hz, exch). [Mass spectrum: +ve ion (ammonia) MH+ (602)].

Provenance & Evidence