反应详情

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1.1 g, 2.23 mmol) in DMSO (10 mL) was added potassium tert-butoxide (1.25 g, 11.1 mmol) and the mixture stirred at rt for 1 h. After completion of reaction (by TLC), water (100 mL) was added, followed by extraction with EtOAc (2×100 mL) and the organic layer then discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with hot EtOAc (3×100 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to obtain the desired product as off-white solid (0.9 g, 87% yield). 1H NMR (DMSO-d6): δ 1.14 (t, J=7.20 Hz, 3H), 1.21 (s, 3H), 1.42 (m, 2H), 2.04 (m, 2H), 3.20 (m, 2H), 3.33 (q, J=7.20, 2H), 4.25 (m, 2H), 4.67 (s, 1H), 6.80 (br s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 8.86 (s, 2H), 10.78 (br s, 1H) and 12.46 (br, s, 1H).

1. additionwas added
2. extractionfollowed by extraction with EtOAc (2×100 mL)
3. extractionextracted with hot EtOAc (3×100 mL)
4. dry with materialthe combined organic layer dried over Na2SO4
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe residue thus obtained
8. customwas triturated with ether