Trifluoroacetic acid → N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamide

HRID 1038428Notes

Reaction equation

HRID 1038428 reaction equation
[C:1]1([CH2:7][S:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19]3[O:20][C:21]([C:24]4[N:25](C(OC(C)(C)C)=O)[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:22][N:23]=3)[CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[C:24]1[C:21]1[O:20][C:19]([NH:18][C:14]2[CH:13]=[C:12]([NH:11][S:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=2)=[N:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060369tert-butyl 2-(2-((3-(phenylmethylsulfonamido)phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

Product 1

HCID 71060426N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 2-(2-((3-(phenylmethylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 28 (0.24 g, 0.441 mmol) in anhydrous CH2Cl2 (20 mL) was added 1:1 mixture of CH2Cl2:Trifluoroacetic acid (10 mL) at room temperature. Reaction was stirred for 1.5 hour at ambient temperature. It was quenched with aq. saturated NaHCO3 and CH2Cl2 layer was separated. After evaporation of solvent, crude product was purified using MPLC silica column (Biotage) (Acetone/hexane as an eluent) to obtain N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamide 29 (0.14 g, 71% yield).

Workup

  1. customat room temperature
  2. customReaction
  3. customIt was quenched with aq. saturated NaHCO3 and CH2Cl2 layer
  4. customwas separated
  5. customAfter evaporation of solvent, crude product
  6. customwas purified

Sources & evidence

ORD record
ord-66f17183c4cc47d1a0f06158e4eb687b
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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