Sodium hydride → tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Compound 353 (270 mg, 0.87 mmol), 2-nitro-5-(thiophen-2-yl)benzenamine (3, 193 mg, 0.87 mmol), and BOP (386 mg, 0.87 mmol) were dissolved in dry pyridine (10 mL). Sodium hydride (140 mg, 3.50 mmol) was added and the resulting solution was stirred at room temperature for 2 hours, quenched with glacial acetic acid (1 mL), and the pyridine was removed under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The extract was dried with sodium sulphate and evaporated to yield a residue which was triturated with ethyl acetate for 15 minutes, to afford the title compound 354 as a yellow solid (270 mg, 61% yield). 1H NMR: (DMSO) δ 10.79 (s, 1H), 8.06-8.04 (m, 2H), 7.86 (d, J=3.9 Hz, 1H), 7.75-7.68 (m, 3H), 7.25-7.20 (m, 2H), 6.32 (s, 1H), 4.04-4.01 (m, 2H), 3.54 (t, J=5.3 Hz, 2H), 1.43 (s, 9H).

1. customquenched with glacial acetic acid (1 mL)
2. customthe pyridine was removed under reduced pressure
3. additionWater (50 mL) was added
4. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
5. dry with materialThe extract was dried with sodium sulphate
6. customevaporated
7. customto yield a residue which
8. customwas triturated with ethyl acetate for 15 minutes

ORDレコード

ord-0045b27329f443adb567b91163174734

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07868205B2