4-(1,1-Difluoropropan-2-yl)benzene-1-sulfonyl chloride → HCID 67071452, compound

HRID 1260253Notes

Reaction equation

HRID 1260253 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][CH:16]([F:29])[CH: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:29][CH:16]([F:15])[CH:17]([C:19]1[CH:20]=[CH:21][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:23][CH:24]=1)[CH3:18]

Participants

4

Reactant 2

HCID 468355874-(1,1-Difluoropropan-2-yl)benzene-1-sulfonyl chlorideHCID 57470084HCID 57470084, compound

Product 1

HCID 67071452HCID 67071452, compoundYield 18%

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-(2,2-difluoro-1-methyl-ethyl)-benzenesulfonyl chloride (321 mg, 1.26 mmol). Purification of the crude product by flash column chromatography (CH2Cl2:methanol, 95:5) provided the title compound (40 mg, 18%) as a colourless gum.

Workup

  1. customPurification of the crude product by flash column chromatography (CH2Cl2:methanol, 95:5)

Sources & evidence

ORD record
ord-5f0ce68351114b32af029f2dcb6f900c
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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