Water → HCID 86724157, compound

Participants

Reaction Conditions

Reaction Steps

In an Erlenmeyer flask, 1-methyl-3-nitro-1-nitrosoguanidine (1.20 g, 8.16 mmol, TCI) was added portionwise to 45% KOH (10 mL)/H2O (5 mL) and Et2O (24 mL) at 0° C. The mixture was stirred until the yellow color of the ether layer did not change in intensity. The solution was poured into a separatory funnel and the aqueous layer was drained. The ether layer was poured into an Erlenmeyer flask and then decanted into another to remove some residual water. The yellow ether solution was poured slowly into a solution of 3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoic acid (0.240 g, 0.639 mmol) in THF (12 mL) cooled to about 0° C. in an ice bath. The ice bath was allowed to melt. The mixture was diluted with THF (12 mL) and a nitrogen stream was blown over the surface until the solution turned from yellow to colorless. The mixture was concentrated in vacuo to give methyl 3-methyl-4-(1-methyl-7-oxo-3-(pyridin-2-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-4-yl)benzoate (0.220 g, 88%): LC-MS (Table 1, Method g) Rt=2.09 min, m/z 390 (M+H)+; 1H-NMR (DMSO, Bruker 400 MHz) δ 8.30-8.24 (m, 1H), 7.71-7.64 (m, 2H), 7.62-7.57 (m, 1H), 7.45-7.41 (m, 1H), 7.08-7.01 (m, 1H), 6.73-6.69 (m, 1H), 5.30-5.26 (m, 1H), 4.28-4.17 (m, 1H), 3.96 (d, J=15.6 Hz, 1H), 3.89 (s, 3H), 3.75 (s, 3H), 2.63-2.56 (m, 4H), 2.39-2.30 (m, 2H), 2.19-2.07 (m, 1H).

Provenance & Evidence