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

HRID 2097849Notes

Reaction equation

HRID 2097849 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]([O:25]CC)=O)[C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH2:1]([N:8]1[CH2:22][C:23](=[O:25])[NH:19][C:18]2[CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[N:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7540Triphenyl phosphiteHCID 59416801Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 58324373Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylateYield 71%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 516859Ammonium metavanadateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-(benzyl(2-ethoxy-2-oxoethyl)amino)-5-nitronicotinate (445 mg g, 1.19 mmol) was dissolved in dichloromethane (5 mL). To the yellow solution was added ammonium metavanadate (10.0 mg, 0.085 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (50 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (75 psi) and stirred at room temperature for 48 h. The reaction was then depressurized and diluted with dichloromethane (20 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×10 mL). The filtrate was concentrated to yield the title compound (250 mg, 71%) as a white solid. [M+H] calc'd for C16H15N3O3, 298; found, 298.

Workup

  1. temperaturewas then refluxed for 30 min
  2. filtrationThe hot solution was filtered through a pad of celite
  3. washwashed with hot dichloromethane (3×10 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b22621f24f534efab4a2e8842e3e2ce3
Source dataset
uspto-grants-2013_05
Patent number
US08450323B2

Reaction notes

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