N-[4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenyl]-4-isopropyl-benzenesulfonamide → HCID 60205212, compound

HRID 1260261Notes

Reaction equation

HRID 1260261 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[C:15]([F:32])[CH:14]=2)[CH2:9]1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C.C(O)(=O)C>[F:32][C:15]1[CH:14]=[C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:18]=[CH:17][C:16]=1[NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21]

Participants

5

Reactant 1

HCID 53628720N-[4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenyl]-4-isopropyl-benzenesulfonamide

Product 1

HCID 60205212HCID 60205212, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[4-(1-benzyl-pyrrolidin-3-yl)-2-fluoro-phenyl]-4-isopropyl-benzenesulfonamide (170 mg, 0.31 mmol) and 10% palladium on carbon (20 mg) in ethyl acetate (25 ml) and acetic acid (10 ml) was hydrogenated over night (20% conversion). The reaction mixture was irradiated with an infra-red lamp for 3 h (complete conversion). The catalyst was filtered, and the solvent was removed under vacuum to yield an oil (45 mg, 64% purity, 26%).

Workup

  1. waitwas hydrogenated over night
  2. customThe reaction mixture was irradiated with an infra-red lamp for 3 h (complete conversion)
  3. filtrationThe catalyst was filtered
  4. customthe solvent was removed under vacuum
  5. customto yield an oil (45 mg, 64% purity, 26%)

Sources & evidence

ORD record
ord-a22d2a2e0d644cc58b831c89ab422bce
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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