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

HRID 69670

反応式

HRID 69670 の反応式
C([O:3][C:4](=O)[CH2:5][N:6]([CH:20]([CH3:22])[CH3:21])[C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)C.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH:20]([N:6]1[CH2:5][C:4](=[O:3])[NH:17][C:16]2[CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[N:8][C:7]1=2)([CH3:22])[CH3:21]

参加物

7

反応物 3

HCID 7540Triphenyl phosphiteHCID 58324358Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58324447Methyl 4-isopropyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate収率 93%

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-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinate (2.39 g, 7.35 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (15.0 mg, 1.13 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (240 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (110 psi) and stirred at room temperature for 16 h. The reaction was then depressurized and diluted with dichloromethane (80 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×20 mL). The filtrate was concentrated to yield the title compound (1.70 g, 93%) as a white solid. [M+H] calc'd for C12H15N3O3, 250; found, 250.

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 (3×20 mL)
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-ab433c647ec9410a9b94866b44f2363b
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

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