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Citric Acid → (2S)-N-(5-chloropyridin-2-yl)-3-ethoxy-2-(1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

HRID 1098012
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HRID 1098012 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:18])[C@@H:12]([OH:17])[CH2:13][O:14][CH2:15][CH3:16])=[N:8][CH:9]=1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]2[N:26]([C:29]3[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=3)[N:27]=[CH:28][C:21]=12.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:18])[C@@H:12]([O:17][C:20]2[N:25]=[CH:24][N:23]=[C:22]3[N:26]([C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)[N:27]=[CH:28][C:21]=23)[CH2:13][O:14][CH2:15][CH3:16])=[N:8][CH:9]=1
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HCID 311Citric AcidHCID 24758Sodium hydrideHCID 57504490HCID 57504490, 화합물HCID 575045064-chloro-1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

생성물 1

HCID 57504378(2S)-N-(5-chloropyridin-2-yl)-3-ethoxy-2-(1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide수율 11.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Sodium hydride (21.49 mg, 0.54 mmol) was added to (S)—N-(5-chloropyridin-2-yl)-3-ethoxy-2-hydroxypropanamide (110 mg, 0.45 mmol) in anhydrous THF (5 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes and then 4-chloro-1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (110 mg, 0.45 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was neutralised with 1M citric acid and the majority of the THF removed in vacuo. The reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (2×20 mL). The combined organics were washed with saturated brine (10 mL), dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 5% MeOH in DCM to afford the product (24.0 mg, 11.8%). 1H NMR (400 MHz, CDCl3) δ1.23 (t, 3H), 2.45 (s, 3H), 3.59-3.72 (m, 2H), 4.05-4.16 (m, 2H), 6.06 (t, 1H), 7.31-7.38 (m, 1H), 7.66-7.71 (m, 1H), 7.73-7.78 (m, 1H), 8.21-8.27 (m, 2H), 8.42 (s, 1H), 8.57 (s, 1H), 8.64-8.69 (m, 1H), 8.89 (s, 1H). m/z (ESI+) (M+H)+=454.31; HPLC tR=1.83 min

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 hour
  3. customthe majority of the THF removed in vacuo
  4. additionThe reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer re-extracted with ethyl acetate (2×20 mL)
  7. washThe combined organics were washed with saturated brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe crude product was purified by flash silica chromatography
  11. washeluting with 0 to 5% MeOH in DCM

출처 및 근거

ORD 기록
ord-adbd0fe13fca4754994681266e6e96be
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143263B2

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