Trifluoroacetic acid → Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

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Reaction Steps

Trifluoroacetic acid (10 mL) is added to a solution of 2-(4-benzyloxycarbonyl-2-oxo-piperazin-1-ylmethyl)-4-chloro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (5.66 g, 11.3 mmol, prepared in the same manner as described previously) in CH2Cl2 (10 mL). The solution is stirred overnight then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (3.81 g, 9.56 mmol) as a foamy yellow solid. 1H NMR (CDCl3, 300 MHz) δ9.43 (bs, 1H), 8.08 (d, 1H), 7.38 (s, 5H), 7.18 (d, 1H), 6.51 (s, 1H), 5.15 (s, 2H), 4.58 (s, 2H), 4.20 (s, 2H), 3.71 (m, 2H), 3.50 (m, 2H). Ion spray [M+H]+=399, 401, Cl pattern.

Provenance & Evidence