Trifluoroacetic acid → Ethyl 4-(2-oxo-1,4-dihydropyrido[4,3-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

HRID 501096

반응식

HRID 501096 반응식
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)=O)(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl>[O:12]=[C:13]1[NH:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[CH2:22][N:23]1[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 682631,1'-CarbonyldiimidazoleHCID 22293255Ethyl 4-[(4-[(tert-butoxycarbonyl)amino]pyridin-3-yl methyl)amino]piperidine-1-carboxylate

생성물 1

HCID 22293216Ethyl 4-(2-oxo-1,4-dihydropyrido[4,3-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate수율 46.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (0.50 mL) was a add to a solution of the material from Step A (0.24 g, 0.63 mmol) in dichloromethane (5 mL). After stirring overnight, another 0.5 mL of trifluoroacetic acid was added. After an additional 2 h, the reaction was concentrated. This material was dissolved in acetonitrile (5 mL) and carbonyldiimidazole (0.31 g, 1.89 mmol) was added at room temperature. After 2 h, the acetonitrile was evaporated in vacuo, the residue partitioned between 1N NaOH and dichloromethane, and the organic phase dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 10 to 15% methanol in methylene chloride gradient elution), which gave the title compound (0.089 g). MS 305.3.

후처리

  1. waitAfter an additional 2 h
  2. concentrationthe reaction was concentrated
  3. dissolutionThis material was dissolved in acetonitrile (5 mL)
  4. waitAfter 2 h
  5. customthe acetonitrile was evaporated in vacuo
  6. customthe residue partitioned between 1N NaOH and dichloromethane
  7. dry with materialthe organic phase dried over magnesium sulfate
  8. customThe crude product was purified by chromatography (silica gel, 10 to 15% methanol in methylene chloride gradient elution), which

출처 및 근거

ORD 기록
ord-21ed386069564df4b2e7eccc1328aad0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772224B2

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