Potassium Carbonate → 2,2,2-Trifluoro-N-(4-(2-methoxyphenoxy)phenyl)-N-(3-pyridinylmethyl)ethanesulfonamide

HRID 392401Notes

Reaction equation

HRID 392401 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][CH:7]=1.[F:24][C:25]([F:32])([F:31])[CH2:26][S:27](Cl)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:27]([CH2:26][C:25]([F:32])([F:31])[F:24])(=[O:29])=[O:28])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 109904214-(2-methoxyphenoxy)-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 98250842,2,2-Trifluoro-N-(4-(2-methoxyphenoxy)phenyl)-N-(3-pyridinylmethyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 21470604DCE PyridineSolvent

Procedure

A solution of N-(4-(2-methoxyphenoxy)phenyl)pyridin-3-ylmethylamine (1.0 equiv.) in 2:1 DCE/Pyridine (0.15 M) was cooled to 0° C. and treated with 2,2,2-trifluoroethanesulfonyl chloride (1.8 equiv.). The mixture was allowed to warm to ambient temperature and stir overnight. The reaction was treated with anhydrous potassium carbonate, stirred for 40 min, and filtered. The filtrate was purified via preparative HPLC eluting with 98:2 to 96:4 DCM/MeOH to give the title compound. Anal Calcd for C21H19F3N2O4S: C, 55.75; H, 4.23; N, 6.19. Found: C, 55.65; H, 4.27; N, 6.19. MS found 4.53.0 [M+H]+

Workup

  1. stirringstirred for 40 min
  2. filtrationfiltered
  3. customThe filtrate was purified via preparative HPLC
  4. washeluting with 98:2 to 96:4 DCM/MeOH

Sources & evidence

ORD record
ord-30f3993c84af4b15b988a21505d8ce6c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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