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

HRID 1260249Notes

Reaction equation

HRID 1260249 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][C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH3:18]>C(Cl)Cl.N1C=CC=CC=1>[F:15][CH2:16][C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([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:27])=[O:26])=[CH:21][CH:20]=1)[CH3:18]

Participants

4

Reactant 2

HCID 536286024-((R)-2-Fluoro-1-methyl-ethyl)-benzenesulfonyl chlorideHCID 57470084HCID 57470084, compound

Product 1

HCID 670713324-((R)-2-Fluoro-1-methyl-ethyl)-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamideYield 5%

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 (150 mg, 0.78 mmol) in CH2Cl2/pyridine 1:1 (12 ml) was treated with 4-((R)-2-fluoro-1-methyl-ethyl)-benzenesulfonyl chloride (242 mg, 1.02 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 (15 mg, 5%) 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-6f88832298594a03bb30a7afe99dfb7e
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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