홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Water → 1-{3-[6-Chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-1-oxopropyl}-4-(phenylmethyl)-4-piperidinol

HRID 1016655
노트
인쇄 미리보기

반응식

HRID 1016655 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10](/[CH:20]=[CH:21]/[C:22]([N:24]3[CH2:29][CH2:28][C:27]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([OH:30])[CH2:26][CH2:25]3)=[O:23])=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:12]=2)[CH:9]=1.O>N1C=CC=CC=1.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:20][CH2:21][C:22]([N:24]3[CH2:25][CH2:26][C:27]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([OH:30])[CH2:28][CH2:29]3)=[O:23])=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:12]=2)[CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydride2회HCID 18407035(E)-1-{3-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-1-oxo-2-propenyl}-4-(phenylmethyl)-4-piperidinol

생성물 1

HCID 101421591-{3-[6-Chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-1-oxopropyl}-4-(phenylmethyl)-4-piperidinol

시약·촉매·용매 1

HCID 22021344
Pyridine methanol
용매

실험 절차

Sodium borohydride (30 mg, 0.8 mmol) was added to a solution of (E)-1-{3-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-1-oxo-2-propenyl}-4-(phenylmethyl)-4-piperidinol (Description 20, 40 mg, 0.08 mmol) in pyridine/methanol (3:1, 4 mL) and the mixture was stirred under reflux for 2 h. Further portions of sodium borohydride (30 mg, 0.8 mmol) were added and the reaction was monitored by mass spectrometry until no starting material remained. The mixture was cooled, poured into water (75 mL) and extracted with ethyl acetate (3×25 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (35:65). The residue was recrystallised from ethanol/water and the solid was collected and dried in vacuo to give the title compound as a colorless solid. 1H NMR (360 MHz, CDCl3) δ 8.18 (1H, d, J 1.5 Hz), 7.74 (2H, d, J 8.5 Hz), 7.56 (1H, d, J 9.6 Hz), 7.44 (2H, d, J 8.5 Hz), 7.30 (3H, m), 7.15 (3H, m), 4.40 (1H, m), 3.47 (2H, m), 3.43 (1H, m), 3.24 (1H, m), 2.92 (1H, m), 2.68 (2H, s), 2.64 (2H, t, J 7.5 Hz), 1.46 (2H, m), and 1.24 (2H, m). m/z (ES+) 508, 510 (M+1).

후처리

  1. temperatureunder reflux for 2 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with isohexane/EtOAc (35:65)
  9. customThe residue was recrystallised from ethanol/water
  10. customthe solid was collected
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-3cf3d135450e43a6b10476975c8c9054
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06476045B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트