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

HRID 8366

反応式

HRID 8366 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-38df20f512e84f7faadc91d1b13aecdb
出典データセット
uspto-grants-2006_08
特許番号
US07087757B2

関連ノート

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