HCID 86727369, compound → HCID 86727370, compound

HRID 519013Notes

Reaction equation

HRID 519013 reaction equation
[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][C:27]=2[C:28]([CH3:30])=[CH2:29])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:32])[C:19](=[O:31])[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][C:27]=2[CH:28]([CH3:29])[CH3:30])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:32])[C:19](=[O:31])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86727369HCID 86727369, compound

Product 1

HCID 86727370HCID 86727370, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(7-isopropenyl-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 (0.035 g, 2.76 mmol) in MeOH (15 mL) was added Pd/C (10%, 0.005 g, 0.005 mmol). The reaction mixture was stirred under an H2 atmosphere (50 psi) for 10 h. The catalyst was removed by filtration and washed with methanol (3×5 mL). The filtrate was concentrated in vacuo to give 4-(7-isopropyl-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 (0.035 g, 100%). LC/MS (Table 1, Method 5) Rt=3.554 min.; MS m/z: 443 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-774b40bd552a4e349010cbbba4112adb
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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