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

HRID 501096

反応式

HRID 501096 の反応式
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

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 682631,1'-CarbonyldiimidazoleHCID 22293255Ethyl 4-[(4-[(tert-butoxycarbonyl)amino]pyridin-3-yl methyl)amino]piperidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-21ed386069564df4b2e7eccc1328aad0
出典データセット
uspto-grants-2010_08
特許番号
US07772224B2

関連ノート

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