Sodium borohydride → 3-[3-(Hydroxymethyl)-4-[1-methyl-6-oxo-5-(pyrazin-2-ylamino)-3-pyridyl]-2-pyridyl]-6,7,8,9-tetrahydrobenzothiopheno[2,3-d]pyridazin-4-one

온도

30 °C

A mixture of 194b (200 mg, 0.4 mmol) and NaBH4 (48 mg, 1.2 mmol) in methanol (20 mL) was stirred at 30° C. for 2 h. The mixture was quenched with water (5 mL) and concentrated under reduced pressure. The residue was extracted with ethyl acetate (3×10 mL). The combined with ethyl acetate extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 194 (60 mg, 30%) as a white solid. MS-ESI: [M+H]+ 514.2. 1H NMR (500 MHz, CDCl3) δ 8.78 (d, J=2.0 Hz, 1H), 8.69 (d, J=5.0 Hz, 1H), 8.31 (s, 1H), 8.29 (s, 1H), 8.17 (s, 1H), 8.13 (s, 1H), 8.04 (d, J=2.5 Hz, 1H), 7.83 (d, J=2.5 Hz, 1H), 7.56 (d, J=5 Hz, 1H), 4.44-4.37 (m, 3H), 3.76 (s, 3H), 3.01-2.99 (m, 2H), 2.88-2.86 (m, 2H), 2.01-1.96 (m, 4H).

1. customThe mixture was quenched with water (5 mL)
2. concentrationconcentrated under reduced pressure
3. extractionThe residue was extracted with ethyl acetate (3×10 mL)
4. extractionextract
5. concentrationwas concentrated under reduced pressure
6. customthe residue was purified by reverse-phase prep-HPLC

ORD 기록

ord-10c316d8d4be4f1fbc342c310a07d43f

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08716274B2