Methanesulfonyl chloride → N-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-methanesulfonamide

HRID 1097935Notes

Reaction equation

HRID 1097935 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:27])[C:14]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[CH:21]=2)([OH:19])[C:15]([F:18])([F:17])[F:16])=[C:9]([Cl:28])[CH:8]=1>N1C=CC=CC=1>[Cl:28][C:9]1[CH:8]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:12]=[CH:11][C:10]=1[CH:13]([CH3:27])[C:14]([C:20]1[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[CH:21]=1)([OH:19])[C:15]([F:18])([F:17])[F:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 25254770N-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-methanesulfonamideYield 88.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (60 mg) was added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (38 mg) in pyridine (1 ml). The mixture was stirred for 30 min at room temperature. Purification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 20-95% CH3CN in 0.1% HCOOH[aq]) gave the title compound (41 mg) as a white foam. MS (m/e)=443.1 [M+H+].

Workup

  1. customPurification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 20-95% CH3CN in 0.1% HCOOH[aq])

Sources & evidence

ORD record
ord-72d7934a387a432db8bc23aa9962aa87
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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