HCID 66816696, compound → HCID 66818133, compound

HRID 1755025Notes

Reaction equation

HRID 1755025 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([NH2:34])=[O:33])[CH:5]=[CH:6][C:7]=1/[CH:8]=[CH:9]/[S:10]([N:13]1[CH2:30][CH2:29][C:16]2([N:20]=[C:19]([CH:21]3[CH2:26][CH2:25][CH:24]([CH3:27])[CH2:23][CH2:22]3)[NH:18][C:17]2=[O:28])[CH2:15][CH2:14]1)(=[O:12])=[O:11].[H][H]>C(#N)C.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([NH2:34])=[O:33])[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][S:10]([N:13]1[CH2:14][CH2:15][C:16]2([N:20]=[C:19]([CH:21]3[CH2:22][CH2:23][CH:24]([CH3:27])[CH2:25][CH2:26]3)[NH:18][C:17]2=[O:28])[CH2:29][CH2:30]1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 66816696HCID 66816696, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66818133HCID 66818133, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

20% palladium hydroxide (7.4 mg) was added to a solution of Compound 737 (14.7 mg, 0.030 mmol) in acetonitrile (1.0 mL), and the mixture was stirred at room temperature for one hour in a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 2-(3-methyl-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-acetamide (Compound 750) as a white powder (10.6 mg, 72%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-546ad4c8b97147bfa5d14e00629716dd
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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