N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamide → 2-[4'-[3-(Pyrrolidino)propylamino]phenyl]-8-methylimidazo[1,2-a]pyridine

A mixture of the product of Step C (122 mg) and borane-methylsulfide complex (0.5 mL of a 2M solution in toluene) in toluene (3.5 mL) was stirred and heated at reflux for 18 hours. The mixture was cooled to ambient temperature and evaporated. The residue was treated with 1 M HCl (10 mL) and heated to reflux. The aqueous mixture was cooled to ambient temperature and treated with solid sodium hydroxide until the pH of the mixture was 8. The aqueous mixture was extracted three times with dichloromethane (10 mL each). The combined organic layers were dried over sodium sulfate, decanted and evaporated. The residue was purified via silica gel chromatography (methanol/dichloromethane) to yield the title compound (60 mg). 1H-NMR (CD3OD) δ 8.16 (d, J=7.0 Hz, 1H), 7.90 (s, 1H), 7.72 (m, 2H), 7.00 (m, 1H), 6.71 (m, 3H), 3.16 (t, J=7.0 Hz, 2H), 2.59 (m, 9H), 1.86 (m, 2H), 1.65 (m, 4H), 1.50 (m, 2H)

1. temperatureheated
2. temperatureat reflux for 18 hours
3. customevaporated
4. additionThe residue was treated with 1 M HCl (10 mL)
5. temperatureheated to reflux
6. temperatureThe aqueous mixture was cooled to ambient temperature
7. additiontreated with solid sodium hydroxide until the pH of the mixture
8. extractionThe aqueous mixture was extracted three times with dichloromethane (10 mL each)
9. dry with materialThe combined organic layers were dried over sodium sulfate
10. customdecanted
11. customevaporated
12. customThe residue was purified via silica gel chromatography (methanol/dichloromethane)

ORDレコード

ord-c18d3e97c5724b9aac901e6df9b9ef29

出典データセット

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06908929B2