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

HRID 1824499

반응식

HRID 1824499 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]([F: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]([F:22])[CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

3

반응물 2

HCID 8082PiperidineHCID 220156172-(4'-Chloropropoxy-2'fluorophenyl)-7-methylimidazo[1,2-a]pyridine

생성물 1

HCID 220156412-[2-Fluoro-4-(3-piperidin-1-yl-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridine

실험 절차

The product of Step C (118 mg) and piperidine (1.5 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 and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (130 mg). 1H-NMR (CD3OD) δ 8.22 (d, J=8.0 Hz, 1H), 7.98 (m, 2H), 7.27 (s, 1H), 6.76 (m, 3H), 4.00 (t, J=6.0 Hz, 2H), 2.48 (m, 6H), 2.38 (s, 3H), 1.96 (m, 2H), 1.61 (m, 4H), 1.47 (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. customevaporated
  4. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-2da88f145f234ae79e941161c2715148
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041827B2

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