Trifluoroacetic acid → 4-Amino-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644627Notes

Reaction equation

HRID 1644627 reaction equation
FC(F)(F)C(O)=O.COC1C=C(OC)C=CC=1C[NH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)(=[O:22])=[O:21])=[C:16]([F:29])[CH:15]=1>C(Cl)Cl>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)(=[O:22])=[O:21])=[C:16]([F:29])[CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575512544-(2,4-Dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 575512254-Amino-2-fluoro-N-thiazol-2-yl-benzenesulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8 mL, 0.1 mol) was added to the mixture of the [A] 4-(2,4-dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (2.59 g, 0.00612 mol) in methylene chloride (33 mL). The reaction mixture was stirred for one hour (turned into a purple solution) then concentrated to give the crude product, which was purified using Gilson preparative HPLC (reverse phase, Phenomenex 250×30 mm, 15 micron C18 column, 40 mL/min. Gradient, 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8) to give the product as a yellow solid (0.92 g, 55%).

Workup

  1. concentrationthen concentrated
  2. customto give the crude product, which
  3. customwas purified
  4. customGilson preparative HPLC (reverse phase, Phenomenex 250×30 mm, 15 micron C18 column, 40 mL/min. Gradient, 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8)

Sources & evidence

ORD record
ord-1c419206897e4a97b08ef351173c6dba
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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