HCID 86727405, compound → HCID 86727408, compound

HRID 519042Notes

Reaction equation

HRID 519042 reaction equation
[CH2:1]([CH:8]1[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:11]=[C:10]([C:21]2[CH:22]=[CH:23][C:24]3[O:35][CH2:34][C:27]4=[N:28][NH:29][C:30](=[O:33])[CH:31]([CH3:32])[N:26]4[C:25]=3[CH:36]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([CH:8]1[CH2:9][CH:10]([C:21]2[CH:22]=[CH:23][C:24]3[O:35][CH2:34][C:27]4=[N:28][NH:29][C:30](=[O:33])[CH:31]([CH3:32])[N:26]4[C:25]=3[CH:36]=2)[CH2:11][CH2:12][N:13]1[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86727405HCID 86727405, compound

Product 1

HCID 86727408HCID 86727408, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 6-benzyl-4-(1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.147 g, 0.3 mmol) in MeOH (30 mL) was added Pd/C (10%, 0.096 g, 0.1 mmol) and the mixture was stirred under an atmosphere of H2 (50 psi) for 12 h. After filtration, the filtrate was concentrated in vacuo to give tert-butyl 2-benzyl-4-(1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.147 g), which was used in the next step without further purification. LC/MS (Table 1, Method 2) Rt=2.453 min; MS m/z: 491 [M+H]+.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-20d8daa9cf85446996ada05297f8b204
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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