Trifluoroacetic acid → HCID 178523407, compound

HRID 1639559Notes

Reaction equation

HRID 1639559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([O:12][C:13]1[CH:40]=[CH:39][C:16]2[NH:17][C:18]([NH:20][C:21]([NH:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[O:22])=[N:19][C:15]=2[CH:14]=1)(=[O:11])=[O:10].FC(F)(F)C(O)=O>ClCCl.C(OC(C)C)(C)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([O:12][C:13]1[CH:40]=[CH:39][C:16]2[NH:17][C:18]([NH:20][C:21](=[O:22])[NH:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[N:19][C:15]=2[CH:14]=1)(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178452333HCID 178452333, compound

Product 1

HCID 178523407HCID 178523407, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 340 mg of tert-butyl 4-(2-{[(5-{[(2,6-dichlorophenyl)sulfonyl]oxy}-1H-benzimidazol-2-yl)carbamoyl]amino}ethyl)-piperazine-1-carboxylate in 60 cm3 of dichloromethane are added 631 mg of trifluoroacetic acid. The mixture is stirred for 24 hours at a temperature in the region of 20° C., and 590 mg of trifluoroacetic acid are then added. The reaction medium is stirred for three days and then evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 25 cm3 of water, brought to pH 9 with potassium carbonate and then extracted with three times 50 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (2 kPa). After flash chromatography on a column of silica [eluent: chloroform/methanol/28% aqueous ammonia (12/6/0.5 by volume)], the resin obtained is solidified in 25 cm3 of diisopropyl ether, filtered, washed with three times 2 cm3 of diisopropyl ether and then dried under reduced pressure over phosphorus pentoxide. 165 mg of 2-{[(2-piperazin-1-ylethyl)carbamoyl]amino}-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. additionare then added
  2. customevaporated to dryness under reduced pressure (2 kPa)
  3. extractionextracted with three times 50 cm3 of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure (2 kPa)
  7. customAfter flash chromatography on a column of silica [eluent: chloroform/methanol/28% aqueous ammonia (12/6/0.5 by volume)], the resin obtained
  8. filtrationfiltered
  9. washwashed with three times 2 cm3 of diisopropyl ether
  10. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-9ab4b12a5ed247b28d54a8a0dffac1aa
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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