HCID 86727363, compound → HCID 86727365, compound

HRID 519007Notes

Reaction equation

HRID 519007 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][CH:27]=2)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:29])[C:19](=[O:28])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][CH:27]=2)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:29])[C:19](=[O:28])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86727363HCID 86727363, compound

Product 1

HCID 86727365HCID 86727365, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.1 g, 2.76 mmol) in MeOH (15 mL) was added Pd/C (10%, 0.110 g) and the reaction mixture was stirred under H2 (1 atm) for 10 h. The catalyst was removed by filtration, washing with methanol (3×5 mL). The filtrate was concentrated in vacuo to give 4-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.05 g, 100%). LC/MS (Table 1, Method 3) Rt=1.428 min.; MS m/z: 401 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashing with methanol (3×5 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-275d87f76b414c45b43751a81ac3687e
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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