Methane → HCID 54674795, compound

HRID 444965Notes

Reaction equation

HRID 444965 reaction equation
[ClH:1].[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[CH:15][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH:6]1[CH3:30])[CH:3]=[CH2:4].C>C(OCC)(=O)C.[Pd]>[ClH:1].[CH:27]([C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:14]2[CH:15]=[N:16][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH2:2][CH2:3][CH3:4])[CH:6]([CH3:30])[CH2:7]3)=[CH:12][CH:13]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 297MethaneHCID 54674793HCID 54674793, compound

Product 1

HCID 54674795HCID 54674795, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.24 mmol) of N-[6-(4-allyl-3-methylpiperazin-1-yl)pyridin-3-yl]-4-isopropylbenzenesulfonamide hydrochloride from Example 13.4 were dissolved in 10 ml of ethyl acetate, after which 10 mg of palladium on active charcoal (10%) were added and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. After that, the catalyst was filtered off and the filtrate was evaporated down to dryness. After 1 ml of dichloromethane had been added to the resulting residue, diethyl ether was slowly added dropwise until the solution became cloudy. The reaction mixture was stirred for 30 minutes and the precipitate which had formed was filtered off with suction. The filtrate was evaporated down to dryness, after which the residue was dissolved in a 1:1 mixture of dichloromethane and diethyl ether and converted into the hydrochloride by adding ethereal hydrochloric acid. 71 mg (63% of theory) of the title compound were obtained.

Workup

  1. filtrationAfter that, the catalyst was filtered off
  2. customthe filtrate was evaporated down to dryness
  3. additionAfter 1 ml of dichloromethane had been added to the resulting residue, diethyl ether
  4. additionwas slowly added dropwise until the solution
  5. stirringThe reaction mixture was stirred for 30 minutes
  6. customthe precipitate which had formed
  7. filtrationwas filtered off with suction
  8. customThe filtrate was evaporated down to dryness
  9. dissolutionafter which the residue was dissolved in a 1:1 mixture of dichloromethane and diethyl ether
  10. additionby adding ethereal hydrochloric acid

Sources & evidence

ORD record
ord-960794fc98b74565aa5a3b647be5d7d3
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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