Thioglycolic Acid → HCID 57906493, compound

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Reaction Steps

A mixture of {6-(2,4-dichloro-phenyl)-3-[4-(2-nitro-benzenesulfonyl)-piperazin-1-yl]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester (2.9 g, 4.38 mmol, prepared following the procedure described for Example 6, Step 3.3 using the adequate cyclisation reagent), LiOH.H2O (1.11 g, 26.3 mmol) and mercaptoacetic acid (0.94 mL, 13.2 mmol) in DMF (20 mL) was stirred at RT for 30 min then poured into a saturated aqueous NaHCO3 solution (200 mL) and extracted with AcOEt (4×200 mL). The combined organic fractions were washed with brine (100 mL), dried over Na2SO4, filtered and evaporated to dryness. The remaining residue was purified by Combi-Flash CompanionT™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/[DCM/MeOH—NH3 9:1]95:5→100% [DCM/MeOH—NH3 9:1]) to yield the title compound (1.61 g, 3.38 mmol, 77%) as a yellow foam. MS: 477 [M+1]+; HPLC: AtRet=1.45; TLC: RF 0.33 (DCM/MeOH—NH3 9:1).

Provenance & Evidence