HCID 68074178, compound → HCID 66744038, compound

HRID 2364081Notes

Reaction equation

HRID 2364081 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[S:15][C:14]2[C:13](=[O:16])[NH:12][C:11]3([CH2:21][CH2:20][CH:19]([NH:22]C(=O)OCC4C=CC=CC=4)[CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=1>[Pd].[OH-].[OH-].[Pd+2].CO>[NH2:22][CH:19]1[CH2:20][CH2:21][C:11]2([NH:10][C:9]3[CH:8]=[C:7]([C:3]4[CH:4]=[N:5][NH:6][C:2]=4[CH3:1])[S:15][C:14]=3[C:13](=[O:16])[NH:12]2)[CH2:17][CH2:18]1

Participants

5

Reactant 1

HCID 68074178HCID 68074178, compound

Product 1

HCID 66744038HCID 66744038, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl [6′-(5-methyl-1H-pyrazol-4-yl)-4′-oxo-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-thieno[3,2-d]pyrimidin]-4-yl]carbamate (the isomer ratio was 1:1, 78 mg, 0.173 mmol), 10% Pd/C (20 mg, 50% wet) and MeOH (5 mL) was stirred for 1 h at room temperature under H2 atmosphere. Then, 20% palladium hydroxide on carbon (200 mg, 50% wet) was added. After 1 h, the mixture was filtered through a pad of celite, and the celite was washed with MeOH well. The filtrate was concentrated under reduced pressure, and the residue was triturated with MeOH/EtOAc. The precipitate was collected by filtration to afford the title compound (35.3 mg, 64%, a mixture of 1:1 cis/trans isomers) as a white solid:

Workup

  1. waitAfter 1 h
  2. filtrationthe mixture was filtered through a pad of celite
  3. washthe celite was washed with MeOH well
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was triturated with MeOH/EtOAc
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2e747c7d5af14932ad5d2497f0a39b4e
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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