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Piperidine → 7-Methyl-2-[2-methyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

HRID 8370
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HRID 8370 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[C:8]([CH3:22])[CH:7]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[N:23]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]4[CH:21]=3)=[C:8]([CH3:22])[CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1
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참가 물질

3

반응물 2

HCID 8082PiperidineHCID 220156392-(4'-Chloropropoxy-2'-methylphenyl)-7-methylimidazo[1,2-a]pyridine

생성물 1

HCID 102700937-Methyl-2-[2-methyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

실험 절차

The product of Step C (200 mg) and piperidine (2.0 mL) were heated at 100° C. for 2.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and the organic portions combined, washed with brine, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (110 mg). 1H-NMR (CD3OD) δ 8.28 (d, J=7.0 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.31 (s, 1H), 6.84 (s, 1H), 6.79 (m, 2H), 4.04 (t, J=6.0 Hz, 2H), 2.50 (m, 12H), 1.99 (m, 2H), 1.64 (m, 4H), 1.51 (m, 2H)

후처리

  1. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  2. extractionThe aqueous portion was extracted with additional ethyl acetate (10 mL)
  3. washwashed with brine
  4. customevaporated
  5. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-10566c0e50794107a81bcc44b7c8cf04
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087757B2

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