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

HRID 1644911

反応式

HRID 1644911 の反応式
C([O:3][C:4](=O)[C@@H:5]([N:7]([CH:21]([CH3:23])[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]>[CH: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)([CH3:23])[CH3:22]

参加物

6

反応物 2

HCID 7540Triphenyl phosphiteHCID 58324420(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(isopropyl)amino)-5-nitronicotinate

生成物 1

HCID 59416799(S)-methyl 4-isopropyl-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[3,2-b]pyrazine-7-carboxylate収率 94.3%

試薬・触媒・溶媒 3

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

実験手順

(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(isopropyl)amino)-5-nitronicotinate (0.900 g, 2.65 mmol) was dissolved in dichloromethane (10 mL). To this solution was added triphenyl phosphite (3.0 mg, 9.7 umol), ammonium metavanadate (30 mg, 0.265 mmol) and Pt/C (5% wt., 0.120 g). The reaction mixture was hydrogenated at 80 psi at 25° C. for 6 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 to afford the title compounds as a white solid (0.658 g, 94%). 1H NMR (400 MHz, CHLOROFORM-d) δ (ppm): 1.33 (d, J=6.82 Hz, 3H) 1.36-1.41 (m, 6H) 3.90 (s, 3H) 4.34 (q, J=6.65 Hz, 1H) 4.86 (m, 1H) 7.52 (d, J=1.77 Hz, 1H) 8.59 (d, J=1.77 Hz, 1H) 8.73 (br. s., 1H); [M+H] calc'd for C13H17N3O3, 264. found 264.

後処理

  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

出典と根拠

ORDレコード
ord-caa4dae0da66465c8c53d1c612a7dc3d
出典データセット
uspto-grants-2012_02
特許番号
US08124606B2

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