Trifluoromethylsulfonamide → N-(3-{1-[5-Chloro-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-propionyl)-C,C,C-trifluoro-methanesulfonamide

HRID 453326

Reaction equation

HRID 453326 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:28]=1)[CH:7]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16](F)=[O:17])=[N:9]1.[F:29][C:30]([F:36])([F:35])[S:31]([NH2:34])(=[O:33])=[O:32]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:28]=1)[CH:7]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[N:8]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([NH:34][S:31]([C:30]([F:36])([F:35])[F:29])(=[O:33])=[O:32])=[O:17])=[N:9]1

Participants

6

Reactant 2

HCID 79001TrifluoromethylsulfonamideHCID 866672893-{1-[5-Chloro-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-propionyl fluoride

Product 1

HCID 86667288N-(3-{1-[5-Chloro-(4-chloro-benzyloxy)-benzyl]-5-methyl-1H-pyrazol-3-YL}-propionyl)-C,C,C-trifluoro-methanesulfonamideYield 72%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acid fluoride 9 (0.14 g, 0.33 mmol) and DMAP 0.161 g (1.3 mmol) in dry DCM, trifluoromethanesulfonamide 0.147 g (0.98 mmol) was added. The mixture was stirred under a nitrogen atmosphere for 16 hours before diluting with EtOAc. The organic phase was washed with 2M HCl, followed by brine, dried over MgSO4 and evaporated to dryness. The crude acyl sulphonamide 10 was purified on silica to yield 0.13 g as a white solid (72%).

Workup

  1. washThe organic phase was washed with 2M HCl
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe crude acyl sulphonamide 10 was purified on silica

Sources & evidence

ORD record
ord-e0210d42a02c48f8befebabf8b50faf8
Source dataset
uspto-grants-2013_07
Patent number
US08492424B2

Linked notes

Loading…