Ethanol → HCID 54767344, 화합물

HRID 1042631노트

반응식

HRID 1042631 반응식
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][NH:10][C:9]3=[O:15])[CH:4]=[CH:3][CH:2]=1.[CH3:16][CH2:17][OH:18]>[Ni]>[OH:18][C@H:17]1[CH2:12][CH2:13][CH2:8][CH2:7][C@@H:16]1[N:10]1[CH:11]=[CH:12][C:13]2[C:8](=[CH:7][C:6]([CH2:6][C:5]3[CH:14]=[N:1][CH:2]=[CH:3][CH:4]=3)=[C:5]3[C:14]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[C:9]1=[O:15]

참가 물질

4

반응물 2

HCID 702EthanolHCID 217862161,8-Phenanthrolin-7(8H)-one

생성물 1

HCID 54767344HCID 54767344, 화합물

시약·촉매·용매 1

HCID 935Nickel촉매2회

실험 절차

A solution of 8-[(1S,2S)-2-hydroxycyclohexyl]-5-{[6-methylsulfanyl)pyridin-3-yl]methyl}-1,8-phenanthrolin-7(8H)-one (40 mg, 0.093 mmol) in EtOH (1.9 mL) was treated with 0.22 g of Raney nickel slurry and heated at reflux for 3 h. Additional Raney nickel slurry (0.25 g) was added and heating continued for 1 hour (h). The gray suspension was filtered through Celite. The resulting filtrate was concentrated and dried in vacuo. The crude material was purified via silica gel chromatography, eluting with 25-100% ethyl acetate in hexanes, followed by elution with 0-15% MeOH in CH2Cl2. The resultant off-white solid gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 386.0 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.95 (dd, J=4.4, 1.6 Hz, 1H), 8.55 (d, J=1.6 Hz, 1H), 8.42 (dd, J=4.4, 1.2 Hz, 1H), 8.21 (s, 1H), 8.13 (dd, J=8.4, 1.6 Hz, 1H), 7.90 (d, J=7.2 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.44 (dd, J=8.4, 4.0 Hz, 1H), 7.34-7.36 (m, 1H), 7.11 (dd, J=8.0, 4.8 Hz, 1H), 4.97 (br s, 1H), 4.39 (s, 2H), 3.90 (br s, 1H), 2.25-2.30 (m, 1H), 2.00-2.04 (m, 1H), 1.87 (d, J=8.0 Hz, 1H), 1.69-1.78 (m, 1H), 1.37-1.64 (m, 3H).

후처리

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. temperatureheating
  4. filtrationThe gray suspension was filtered through Celite
  5. concentrationThe resulting filtrate was concentrated
  6. customdried in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 25-100% ethyl acetate in hexanes
  9. washfollowed by elution with 0-15% MeOH in CH2Cl2
  10. customThe resultant off-white solid gave a proton NMR spectra consistent with theory

출처 및 근거

ORD 기록
ord-a08fd3b9df6d4cb9bca87600d65256ef
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557992B2

반응 노트

불러오는 중…