Sodium borohydride → 2-{3'-Hydroxymethyl-1-methyl-5-[5-(4-oxetan-3-yl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-[3,4']bipyridinyl-2'-yl}-3,4,5,6,7,8-hexahydro-2H-benzo[4,5]thieno[2,3-c]pyridin-1-one

A mixture of 169b (45 mg, 0.070 mmol), NaBH4 (8 mg, 0.21) and methanol (5 mL) was stirred at room temperature for 1 h. The reaction mixture was quenched with water (5 mL) and concentrated under reduced pressure. The residue was extracted with dichloromethane (2×10 mL). The combined dichloromethane extract was concentrated under reduced pressure. The residue was purified with reverse-phase prep-HPLC to afford 169 (14 mg, 30%). LCMS-ESI: [M+H]+ 654. 1H NMR (500 MHz, DMSO-d6) δ 8.62 (s, 1H), 8.50 (d, J=2.0 Hz, 1H), 8.43 (s, 1H), 7.86 (d, J=4.5 Hz, 1H), 7.45 (d, J=2.5 Hz, 1H), 7.39-7.34 (m, 2H), 7.25-7.22 (m, 1H), 4.95-4.93 (m, 1H), 4.57-4.55 (m, 2H), 4.47-4.41 (m, 4H), 4.19-4.17 (m, 1H), 3.82-3.80 (m, 1H), 3.60 (s, 3H), 3.45-3.43 (m, 1H), 3.32-3.30 (m, 1H), 3.09-3.07 (m, 4H), 3.01-2.90 (m, 1H), 2.89-2.88 (m, 1H), 2.80-2.79 (m, 2H), 2.51-2.50 (m, 1H), 2.40-2.38 (m, 4H), 1.83-1.80 (m, 4H).

1. customThe reaction mixture was quenched with water (5 mL)
2. concentrationconcentrated under reduced pressure
3. extractionThe residue was extracted with dichloromethane (2×10 mL)
4. extractionThe combined dichloromethane extract
5. concentrationwas concentrated under reduced pressure
6. customThe residue was purified with reverse-phase prep-HPLC

ORD 기록

ord-7b04c1dc37c847868d2247b05dafe3a4

출처 데이터셋

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08921353B2