Triphenyl phosphite → Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate

HRID 69648

反応式

HRID 69648 の反応式
[CH2:1]([N:8]([CH2:22][C:23]([O:25]CC)=O)[C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH2:1]([N:8]1[CH2:22][C:23](=[O:25])[NH:19][C:18]2[CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[N:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 7540Triphenyl phosphiteHCID 59416801Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58324373Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate収率 71%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 516859Ammonium metavanadate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinate (445 mg g, 1.19 mmol) was dissolved in dichloromethane (5 mL). To the yellow solution was added ammonium metavanadate (10.0 mg, 0.085 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (50 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (75 psi) and stirred at room temperature for 48 h. The reaction was then depressurized and diluted with dichloromethane (20 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×10 mL). The filtrate was concentrated to yield the title compound (250 mg, 71%) as a white solid. [M+H] calc'd for C16H15N3O3, 298; found, 298.

後処理

  1. temperaturewas then refluxed for 30 min
  2. filtrationThe hot solution was filtered through a pad of celite
  3. washwashed with hot dichloromethane (3×10 mL)
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-a6c2a1d20e874012b3a7f0e995912085
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

関連ノート

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