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

HRID 2097872

반응식

HRID 2097872 반응식
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]

참가 물질

7

반응물 3

HCID 7540Triphenyl phosphiteHCID 58324358Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매2회

실험 절차

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 C, 12; H, 15; N, 3; O, 3, 250; found, 250.

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

출처 및 근거

ORD 기록
ord-9b4af75eef554ce499a154c3b2d13bbf
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450323B2

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