HCID 66817420, compound → HCID 66816725, compound

HRID 1755005Notes

Reaction equation

HRID 1755005 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:32][C:33](=[O:35])[CH3:34])[CH:6]=[CH:7][C:8]=1/[CH:9]=[CH:10]/[S:11]([N:14]1[CH2:31][CH2:30][C:17]2([N:21]=[C:20]([CH:22]3[CH2:27][CH2:26][CH:25]([CH3:28])[CH2:24][CH2:23]3)[NH:19][C:18]2=[O:29])[CH2:16][CH2:15]1)(=[O:13])=[O:12].[H][H]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:32][C:33](=[O:35])[CH3:34])[CH:6]=[CH:7][C:8]=1[CH2:9][CH2:10][S:11]([N:14]1[CH2:15][CH2:16][C:17]2([N:21]=[C:20]([CH:22]3[CH2:23][CH2:24][CH:25]([CH3:28])[CH2:26][CH2:27]3)[NH:19][C:18]2=[O:29])[CH2:30][CH2:31]1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 66817420HCID 66817420, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66816725HCID 66816725, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20% Pd(OH)2—C (30 mg) was placed into a solution of N-(3-methoxy-4-{(E)-2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-acetamide (31 mg, 0.0617 mmol) in methanol (5 ml), and the atmosphere was replaced with hydrogen. The mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered, and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give N-(3-methoxy-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-acetamide (20 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-ca788972c6cc4c71a36f6ed058dff9df
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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