Pyridine → HCID 86638587, compound

HRID 1807810Notes

Reaction equation

HRID 1807810 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[N+:24]([C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)([O-:26])=[O:25].N1C=CC=CC=1>ClCCl>[F:23][C:2]([F:22])([F:1])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([S:33]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([N+:24]([O-:26])=[O:25])[CH:28]=3)(=[O:34])=[O:35])[CH2:20][CH2:21]2)=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Product 1

HCID 86638587HCID 86638587, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (2.366 mmol, 810 mg), 3-nitrobenzene-1-sulfonyl chloride (2.366 mmol, 524 mg) and pyridine (4.73 mmol, 0.383 mL, 374 mg) were combined in dichloromethane (20 mL) and stirred at room temperature for 1 hour. The reaction mixture was washed with water, and the organic layer was separated, dried and concentrated under vacuum. The residue was purified by SCX chromatography to afford the title compound (875.3 mg). MS (ESI) m/z 528.0 [M+H]+

Workup

  1. washThe reaction mixture was washed with water
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by SCX chromatography

Sources & evidence

ORD record
ord-e5e66da1e1274f31a572868af1fd973b
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…