Trifluoroacetic acid → HCID 86646946, compound

HRID 1929349Notes

Reaction equation

HRID 1929349 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:10]=1[CH:17]([O:19][C:20]1[C:45]([F:46])=[CH:44][C:23]2[N:24]=[C:25]([NH:27][C:28](=[O:43])[CH2:29][N:30]3[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]3)[S:26][C:22]=2[CH:21]=1)[CH3:18].C(=O)([O-])O.[Na+]>ClCCl.C(#N)C>[Cl:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:10]=1[CH:17]([O:19][C:20]1[C:45]([F:46])=[CH:44][C:23]2[N:24]=[C:25]([NH:27][C:28](=[O:43])[CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[S:26][C:22]=2[CH:21]=1)[CH3:18]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86646947HCID 86646947, compound

Product 1

HCID 86646946HCID 86646946, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

add 0.73 cm3 of trifluoroacetic acid to a solution of 0.385 g of 1,1-dimethylethyl 4-[2-({6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-yl}amino)-2-oxoethyl]piperazine-1-carboxylate in 45 cm3 of dichloromethane. Stir for 16 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 15 cm3 of water. The mixture obtained is adjusted to pH 8-9 with an aqueous solution of sodium hydrogen carbonate and then extracted three times with 40 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 acetonitrile, filtered and then dried under reduced pressure. We obtain 0.178 g N-{6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-fluoro-1,3-benzothiazol-2-yl}-2-(piperazin-1-yl)acetamide in the form of a cream-coloured 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 40 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-7c2107618f5a49fd8a0f9f5b2b7f30e1
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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