HCID 22476603, compound → HCID 22476564, compound

HRID 2184393Notes

Reaction equation

HRID 2184393 reaction equation
[F:1][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]>C(O)C.[Pd]>[F:1][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:11]

Participants

4

Reactant 1

HCID 22476603HCID 22476603, compound

Product 1

HCID 22476564HCID 22476564, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[2-Fluoro-2-(4-nitrophenyl)cyclohexyl][(methylethyl)sulfonyl]amine (prepared in example 6) is diluted with ethanol and was transferred to a Parr bottle containing 1.25 g of 5% Pd on C (rinsed in with 5 mL of THF) under nitrogen (total ethanol=45 mL). The reaction mixture is then hydrogenated for 16-20 hours at 20-25° C. The reaction mixture is then filtered and the filtrate concentrated under vacuum. The residue can then be purified by flash chromatography on silica gel with ethyl acetate/hexanes to provide the final title compound.

Workup

  1. washon C (rinsed in with 5 mL of THF) under nitrogen (total ethanol=45 mL)
  2. filtrationThe reaction mixture is then filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue can then be purified by flash chromatography on silica gel with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-886daf4ecca34e929d32aa657c08f565
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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