HCID 74928750, compound → 17-Cyclohexyl-18-(furan-3-yl)-1,4,11-triaza-tricyclo[11.5.2.016,19]icosa-13(20),14,16(19),17-tetraene-3,12-dione

HRID 39041Notes

Reaction equation

HRID 39041 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]4[C:12](=[O:33])[NH:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][NH:20][C:21](=[O:32])[CH2:22][N:23]([C:30]=3[CH:31]=4)[C:24]=2[C:25]2[CH:29]=[CH:28][O:27][CH:26]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.C1COCC1.[Pd]>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]4[C:12](=[O:33])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:32])[CH2:22][N:23]([C:30]=3[CH:31]=4)[C:24]=2[C:25]2[CH:29]=[CH:28][O:27][CH:26]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 74928750HCID 74928750, compound

Product 1

HCID 4412918617-Cyclohexyl-18-(furan-3-yl)-1,4,11-triaza-tricyclo[11.5.2.016,19]icosa-13(20),14,16(19),17-tetraene-3,12-dioneYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 (30 mg, 0.067 mmol) and 10% Pd/C (20 mg) in methanol (10 mL) and THF (10 mL) was shaken in a hydrogenation apparatus under 55 psi pressure at room temperature for 1 h. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to dryness. Filtration on silica gel afforded 24 mg (80%) of the target product 2: m/z=448 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated to dryness
  4. filtrationFiltration on silica gel

Sources & evidence

ORD record
ord-769ee51495e045eaa102f40047c490c2
Source dataset
uspto-grants-2013_09
Patent number
US08524716B2

Reaction notes

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