Sodium bis(trimethylsilyl)amide → HCID 59623745, compound

Participants

Reaction Steps

To a solution of 3-[(2,2-difluoro-ethyl)-methoxycarbonylmethanesulfonyl-amino]-pyrazine-2-carboxylic acid methyl ester (Example 9.2) (0.819 g) in tetrahydrofuran (40 ml) under nitrogen atmosphere was added in portions a solution of sodium hexamethyldisilazide (“NaHMDS”) (5.8 ml) (1M in THF) at ambient temperature. The reaction mixture was stirred for 3 hours at ambient temperature. The reaction was quenched by addition of glacial acetic acid and the mixture was concentrated. The residue was partitioned between ethyl acetate (30 ml) and aqueous hydrochloric acid (2M) (15 ml). The phases were separated and the organic layer was concentrated to give 1-(2,2-difluoro-ethyl)-4-hydroxy-2,2-dioxo-1,2-dihydro-2-λ-6-thia-1,5,8-triaza-naphthalene-3-carboxylic acid methyl ester (0.520 g). 1H-NMR (400 MHz, CDCl3): 8.65 (d, 1H), 8.59 (d, 1H), 6.02-6.32 (m, 1H), 4.60-4.67 (m, 2H), 4.13 (s, 3H) ppm.

Provenance & Evidence