Methanol → HCID 136348443, compound

Participants

Reaction Steps

A mixture of ethyl 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylbenzoate (5.0 g, 11.8 mmol, prepared using B from Example #2, Step A with ethyl hydrazine oxalate, C with 4-bromo-2-methylbenzaldehyde (Asta Tech) and 2-mercaptoacetic, D with borane-THF complex, E with PdCl2(dppf), TEA, DMF and EtOH), NaOH (0.95 g, 23.6 mmol), THF (30 mL), MeOH (30 mL) and water (15 mL) was stirred at rt for about 3 h. The organic volatiles were removed under reduced pressure. The aqueous layer was adjusted to about pH 6 by the addition of 1N aqueous HCl. The precipitate was collected by filtration and dried under reduced pressure to afford 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylbenzoic acid (4.5 g, 11.4 mmol, 96%) as a white solid. LC-MS (Table 1, Method 1) Rt=1.15 min, m/z 395 (M+H)+.

Provenance & Evidence