Triphenyl phosphite → (S)-methyl 4-ethyl-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate

HRID 69612

반응식

HRID 69612 반응식
C([O:3][C:4](=O)[C@@H:5]([N:7]([CH2:21][CH3:22])[C:8]1[C:17]([N+:18]([O-])=O)=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=1)[CH3:6])C.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH2:21]([N:7]1[C@@H:5]([CH3:6])[C:4](=[O:3])[NH:18][C:17]2[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[N:9][C:8]1=2)[CH3:22]

참가 물질

6

반응물 2

HCID 7540Triphenyl phosphiteHCID 58324496(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(ethyl)amino)-5-nitronicotinate

생성물 1

HCID 59416791(S)-methyl 4-ethyl-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate수율 57.3%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매

실험 절차

(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(ethyl)amino)-5-nitronicotinate (1.22 g, 3.92 mmol) was dissolved in dichloromethane (12 mL). To this solution were added triphenyl phosphite (5.0 mg, 16 umol), ammonium metavanadate (50.0 mg, 0.427 mmol) and Pt/C (5% wt., 0.200 g). The reaction mixture was hydrogenated at 100 psi at 25° C. for 18 h. The mixture was filtered through a small pad of celite and the pad was washed with dichloromethane (20 mL). The combined filtrates were concentrated in vacuo and crystallized with ethyl ether (50 mL) to afford the title compound as a white solid (0.560 g, 57%). [M+H] calc'd for C12H15N3O3, 250; found, 250.

후처리

  1. filtrationThe mixture was filtered through a small pad of celite
  2. washthe pad was washed with dichloromethane (20 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customcrystallized with ethyl ether (50 mL)

출처 및 근거

ORD 기록
ord-775ec1dd130c4113987685689fe418f1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822470B2

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