Water → 3-Amino-7-(2-chlorophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carbonitrile

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Reaction Conditions

Reaction Steps

Chloroacetonitrile (0.35 mL, 5.5 mmol) was added to a solution of Example 2 (1.42 g, 5.0 mmol) in MeCN (50 mL) and the mixture heated at 40° C. for 3 h. H2O (100 mL) was added and the mixture concentrated in vacuo to remove some of the MeCN (remaining volume ˜120 mL). The mixture was cooled to 0° C. and the solid filtered off, washed with H2O (15 mL) and Et2O (2×15 mL) and dried to give the title compound as a pale brown solid (505 mg, 32%). δH (DMSO-d6) 8.10 (1H, d, J 9.7 Hz), 7.75-7.73 (1H, m), 7.65-7.54 (3H, m), 7.14 (2H, br s, NH2), 6.54 (1H, d, J 9.7 Hz). LCMS (ES+) RT 2.97 minutes, 302 (M+H)+.

Provenance & Evidence