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

HRID 1072024

반응식

HRID 1072024 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)[CH:9]=[CH:10][CH:11]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:20][C:18]1[CH:17]=[CH:16][N:15]2[CH:21]=[C:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:7]=3)[N:13]=[C:14]2[CH:19]=1

참가 물질

3

반응물 2

HCID 8082PiperidineHCID 220156092-[3-(3-Chloro-propoxy)-phenyl]-7-methyl-imidazo[1,2-a]pyridine

생성물 1

HCID 220156027-Methyl-2-[3-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

실험 절차

The product of Step C (271 mg) and piperidine (2.0 mL) were heated at 100° C. for 2 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 a fresh portion of ethyl acetate (10 mL) and the organic portions combined and washed with brine (10 mL). The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (193 mg). 1H-NMR (CD3OD) δ 8.27 (d, J=7.0 Hz, 1H), 8.08 (s, 1H), 7.46 (m, 2H), 7.31 (m, 2H), 6.88 (m, 1H), 6.76 (m, 1H), 4.09 (t, J=6.0 Hz, 2H), 2.58 (m, 6H), 2.42 (s, 3H), 2.04 (m, 2H), 1.65 (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 a fresh portion of ethyl acetate (10 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialThe organic portions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-dbdadcfcb55f42c4b58f9a71a508d6c2
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908929B2

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