Potassium Carbonate → 4-[8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine

HRID 456692

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HRID 456692 반응식
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:18](=O)[C:19]#[CH:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH:23]1([NH:28][C:29]([NH2:31])=[NH:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:18]3[CH:19]=[CH:20][N:31]=[C:29]([NH:28][CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:30]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 866010141-[8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, 화합물

생성물 1

HCID 102014694-[8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a solution of 1-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (740 mg, 2.5 mmol) in ethanol (20 mL) was added cyclopentyl guanidine hydrochloride (600 mg, 3.7 mmol), followed by solid potassium carbonate (510 mg, 3.7 mmol). The resulting solution was heated at 80° C. for 12 hours. The reaction mixture was concentrated to a solid. Water and dichloromethane were added. The phases were separated and the organics were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was crystallized from acetonitrile, to give 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (600 mg, 59%) as a white solid. 1H NMR (CDCl3) δ 9.48 (d, 1H), 8.11 (d, 1H), 7.68 (q, 2H), 7.42 (d, 1H), 7.11 (t, 2H), 6.86 (t, 1H), 6.40 (d, 1H), 5.28 (d, 1H), 4.35 (m, 1H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); 19F NMR (CDCl3) δ −113.0; MS m/z 408 (M+1).

후처리

  1. concentrationThe reaction mixture was concentrated to a solid
  2. additionWater and dichloromethane were added
  3. customThe phases were separated
  4. washthe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-4c3e4727dfd14669b613508f75d037a2
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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