Trifluoroacetic acid → HCID 86646942, compound

HRID 1929347Notes

Reaction equation

HRID 1929347 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([Cl:23])[C:17]=1[CH:24]([O:26][C:27]1[CH:54]=[CH:53][C:30]2[N:31]=[C:32]([NH:34][C:35]([NH:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][CH2:41]3)=[O:36])[S:33][C:29]=2[CH:28]=1)[CH3:25].[OH-].[Na+]>ClCCl.C(OC(C)C)(C)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:15][C:16]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([Cl:23])[C:17]=1[CH:24]([O:26][C:27]1[CH:54]=[CH:53][C:30]2[N:31]=[C:32]([NH:34][C:35]([NH:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[O:36])[S:33][C:29]=2[CH:28]=1)[CH3:25]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86646944HCID 86646944, compound

Product 1

HCID 86646942HCID 86646942, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

add 0.376 cm3 of trifluoroacetic acid to a solution of 0.250 g of 1,1-dimethylethyl 4-{2-[({6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1,3-benzothiazol-2-yl}carbamoyl)amino]ethyl}piperazine-1-carboxylate trifluoroacetate in 5 cm3 of dichloromethane. Continue stirring for 4 hours at a temperature close to 20° C. The reaction mixture is then evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 10 cm3 of water. The mixture obtained is adjusted to pH 9 with a 1N solution of sodium hydroxide and then extracted three times with 20 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulphate, then filtered and evaporated to dryness under reduced pressure (2 kPa). The white solid obtained is solidified in 5 cm3 of diisopropyl oxide, filtered and then dried under reduced pressure. We obtain 0.117 g of 1-{6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1,3-benzothiazol-2-yl}-3-(2-piperazin-1-ylethyl)urea trifluoroacetate in the form of a white powder, which has the following characteristics:

Workup

  1. customclose to 20° C
  2. customThe reaction mixture is then evaporated to dryness under reduced pressure (2 kPa)
  3. customThe mixture obtained
  4. extractionextracted three times with 20 cm3 of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (2 kPa)
  8. customThe white solid obtained
  9. filtrationfiltered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-3d22362df4364678a200aa157adba196
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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