2-amino-N,N-dimethylacetamide;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N,N-dimethylglycinamide hydrochloride (5 g) and triethylamine (5.03 mL) in ethanol (20 mL) was added 4-thioxo-1,3-thiazolidin-2-one (4.81 g), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/THF) to give the title compound (4.68 g). The reaction mixture was concentrated the residue was purified by silica gel column chromatography (NH, ethyl acetate/THF)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By General Procedure A from N,N-dimethylglycineamide hydrochloride, triethylamine, and 4-{[(tert-butyldimethylsilyl)oxy]methyl}pyridine-2-carbaldehyde. Purification by column chromatography (0-10% MeOH in DCM) gave the title product as yellow oil. 1H NMR (300 MHz, chloroform-d): δ ppm 8.49 (d, 1H), 7.32 (s, 1H), 7.17 (d, 1H), 4.74 (s, 2H), 3.97 (s, 2H), 3.47 (s, 2H), 2.95 (d, 6H), 0.95 (s, 9H), 0.11 (s, 6H). Purification by column chromatography (0-10% MeOH in DCM)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By General Procedure A from Ethyl 2-formylpyridine-4-carboxylate, N,N-dimethylglycineamide hydrochloride, and triethylamine. Purification by column chromatography with a gradient of 0-10% MeOH in DCM gave the title product as yellow oil. 1H NMR (300 MHz, chloroform-d): δ ppm 8.69 (s, 1H), 7.94 (s, 1H), 7.72 (d, 1H), 4.40 (q, 2H), 4.03 (s, 2H), 3.48 (s, 2H), 2.95 (d, 6H), 1.40 (t, 3H). Purification by column chromatography with a gradient of 0-10% MeOH in DCM