Water → 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-N-phenylpyrimidin-2-amine

HRID 1295879

反応式

HRID 1295879 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19](=O)[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[N+]([O-])([O-])=O.[C:27]1([NH:33][C:34]([NH2:36])=[NH2+:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.CCOCC>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19]3[CH:20]=[CH:21][N:36]=[C:34]([NH:33][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:35]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 112321611-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-oneHCID 178418786HCID 178418786、化合物

生成物 1

HCID 102741414-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-N-phenylpyrimidin-2-amine収率 50%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

To a solution of 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (58 mg, 0.19 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was added N-phenylguanidinium nitrate (185 mg, 0.94 mmol) and potassium carbonate (129 mg, 0.94 mmol). The mixture was heated at 140° C. for 1.25 hours and then cooled to room temperature. Water was added then ether. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes-ethyl acetate) provided 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine (40 mg, 50%) as a yellow solid. 1H NMR (CDCl3 with 2 drops CD3OD): δ 9.45 (d, 1 H), 8.16 (d, 1 H), 7.60–7.58 (m, 2 H), 7.39 (d, 1 H), 7.34–7.29 (m, 3 H), 7.17–7.15 (m, 2 H), 7.07 (t, 1 H), 6.95 (m, 1 H), 6.75 (t, 1 H), 6.58 (d, 1 H), 3.79 (s, 3 H); MS m/z 428 (M+1).

後処理

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organics dried over magnesium sulfate
  5. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-0f2f6b2591e948fd9c25b5ce7a735576
出典データセット
uspto-grants-2007_07
特許番号
US07244740B2

関連ノート

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