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

HRID 2077885

반응식

HRID 2077885 반응식
C[O:2][C:3](=O)[CH2:4][N:5]([CH3:19])[C:6]1[C:15]([N+:16]([O-])=O)=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH3:19][N:5]1[CH2:4][C:3](=[O:2])[NH:16][C:15]2[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[N:7][C:6]1=2

참가 물질

7

반응물 3

HCID 7540Triphenyl phosphiteHCID 58324470Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 58324455Methyl 4-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate수율 68.8%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매2회

실험 절차

Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinate (2.7 g, 9.53 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (30.0 mg, 0.256 mmol), triphenyl phosphite (aprox 30 ul, 0.097 mmol), and Pt/C (300 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 (100 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 in vacuo to yield the title compound (1.45 g, 68%) as a white solid. [M+H] calc'd for C10H11N3O3, 222; found, 222.

후처리

  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 in vacuo

출처 및 근거

ORD 기록
ord-07c42c244d1b434a9301c4ed6f7cb818
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928105B2

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