Trifluoroacetic acid → (E)-N-(2-Amino-phenyl)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylamide

HRID 870075Notes

Reaction equation

HRID 870075 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]1[CH:22]=[CH:21][N:20]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86613977(2-[(E)-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester2×

Product 1

HCID 11545400(E)-N-(2-Amino-phenyl)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylamideYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.116 g of (2-{(E)-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester (compound A5) are dissolved in 20 ml of dichloromethane at ambient temperature. 2 ml of trifluoroacetic acid (TFA) are added and the solution is stirred for 93 hour. The solvent is evaporated to dryness and to the residue are added 25 ml of water. The water phase is extracted exhaustively with ethyl acetate. Afterwards the combined organic phases are dried over sodium sulfate and filtered. The filtrate is evaporated under vacuo. Then the residue is crystallized from methanol to give 0.050 g of the title compound as white crystals.

Workup

  1. customThe solvent is evaporated to dryness and to the residue
  2. additionare added 25 ml of water
  3. extractionThe water phase is extracted exhaustively with ethyl acetate
  4. dry with materialAfterwards the combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated under vacuo
  7. customThen the residue is crystallized from methanol

Sources & evidence

ORD record
ord-6b27e01ae6c343afbae7d981d544aba4
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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