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

HRID 1295879

반응식

HRID 1295879 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
140 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0f2f6b2591e948fd9c25b5ce7a735576
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244740B2

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