4-(2-Fluoroethyl)benzenesulfonyl chloride → 4-(2-Fluoro-ethyl)-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

HRID 1260246Notes

Reaction equation

HRID 1260246 reaction equation
[CH2:1]([N:4]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:5]1)[CH2:2][CH3:3].[F:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl.N1C=CC=CC=1>[F:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:14][C:11]2[CH:10]=[CH:9][C:8]([CH:6]3[CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:7]3)=[CH:13][CH:12]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 234528034-(2-Fluoroethyl)benzenesulfonyl chlorideHCID 57470084HCID 57470084, compound

Product 1

HCID 536286714-(2-Fluoro-ethyl)-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamideYield 6%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

Following the same procedure as described in example 55, 4-(1-propyl-azetidin-3-yl)phenylamine (100 mg, 0.52 mmol) in CH2Cl2/pyridine 9:1 (12 ml) was treated with 4-(2-fluoro-ethyl)-benzenesulfonyl chloride (117 mg, 0.52 mmol). Purification of the crude product by chromatography on reversed phase silica gel (H2O+0.1% acetic acid:CH3CN+0.1% acetic acid, 75:25) provided the title compound (11 mg, 6%) as a colourless gum.

Workup

  1. customPurification of the crude product by chromatography on reversed phase silica gel (H2O+0.1% acetic acid:CH3CN+0.1% acetic acid, 75:25)

Sources & evidence

ORD record
ord-e250ebeb0f4948cfb0209bb2a6daed9a
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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