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

HRID 493610

반응식

HRID 493610 반응식
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=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:17]=[N:18][CH:19]=[CH:20][C:21]=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 acidHCID 682631,1'-CarbonyldiimidazoleHCID 22293284Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

생성물 1

HCID 22293189Ethyl 4-(2-oxo-1,4-dihydropyrido[3,4-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate수율 39.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (1.43 g) was added to a solution of the material from Step A (0.47 g, 1.24 mmol) in dichloromethane (10 mL). After stirring overnight, the reaction was concentrated. This material was dissolved in acetonitrile (5 mL) and carbonyldiimidazole (0.62 g, 3.73 mmol) was added at room temperature. After 2 d, 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, 1 to 20% methanol in methylene chloride gradient elution), which gave the title compound (0.15 g). MS 305.2.

후처리

  1. concentrationthe reaction was concentrated
  2. dissolutionThis material was dissolved in acetonitrile (5 mL)
  3. waitAfter 2 d
  4. customthe acetonitrile was evaporated in vacuo
  5. customthe residue partitioned between 1N NaOH and dichloromethane
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. customThe crude product was purified by chromatography (silica gel, 1 to 20% methanol in methylene chloride gradient elution), which

출처 및 근거

ORD 기록
ord-5d63d910cb6f40239bae1b2e418b6a83
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534784B2

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