[OH:1][C:2]1[C:3]2[S:20][CH:19]=[CH:18][C:4]=2[N:5]([CH3:17])[C:6](=[O:16])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14]C)=[O:13])=[O:9].Cl.NCC(OC)=O.OC1C2SC=CC=2N(C)C(=O)C=1C(OCC)=O>O1CCOCC1>[OH:1][C:2]1[C:3]2[S:20][CH:19]=[CH:18][C:4]=2[N:5]([CH3:17])[C:6](=[O:16])[C:7]=1[C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[O:9]Methyl 2-(7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate. A mixture of methyl 2-aminoacetate hydrochloride (291 mg, 2317 μmol) and ethyl 7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxylate (489 mg, 1931 μmol) in 15 mL dioxane was heated to 100° C. in a sealed tube and stirred for 15 hours. The mixture was cooled to room temperature, and the resulting suspension was added dropwise to 100 mL ice-water. The precipitate was collected by filtration, washed with H2O, and dried in vacuo. The solids were triturated with Et2O, collected by filtration, and dried to give a beige solid. Purification of the crude product by flash chromatography (Gradient from hexanes to hexanes/EtOAc=1:1) gave the title compound as a white solid (301 mg). MS (ESI) m/z: Calculated; 296.3: Observed; 297.1. 1H NMR (300 MHz, CDCl3) δ ppm 10.73 (1H, br. s), 7.78 (1H, d, J=5.3 Hz), 7.08 (1H, d, J=5.3 Hz), 4.24 (2H, br. s), 3.79 (3H, s), 3.69 (3H, s)
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