HCID 86727452, compound → HCID 86727454, compound

HRID 519084Notes

Reaction equation

HRID 519084 reaction equation
[CH2:1]([C@H: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])[C@@H: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]([C@@H: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])[C@@H: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 86727452HCID 86727452, compound

Product 1

HCID 86727454HCID 86727454, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-tert-butyl 6-benzyl-4-((R)-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 (0.330 g, 0.675 mmol) in MeOH (20 mL) was added Pd/C (10%, 0.033 g, 0.028 mmol) and the mixture was stirred under an atmosphere of H2 (50 psi) at 50° C. for 12 h. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo to give crude (2S)-tert-butyl 2-benzyl-4-((R)-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 (0.320 g). LC/MS (Table 1, Method 4) Rt=2.813 min; MS m/z: 513 [M+23]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-999b7173ac05474baf3f33757ee69f03
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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