Trifluoroacetic acid → N-{4-Methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-yl)benzamide

HRID 1055702Notes

Reaction equation

HRID 1055702 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH:14]=[C:15]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])[CH:16]=2)=[O:10])=[CH:4][C:3]=1[N:36]1[C:43]2[N:39]([N:40]=[C:41]([C:44]3[CH:45]=[N:46][NH:47][CH:48]=3)[CH:42]=2)[CH:38]=[CH:37]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[C:11]2[CH:12]=[C:13]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:14]=[C:15]([S:17]([F:20])([F:22])([F:21])([F:18])[F:19])[CH:16]=2)=[CH:4][C:3]=1[N:36]1[C:43]2[N:39]([N:40]=[C:41]([C:44]3[CH:45]=[N:46][NH:47][CH:48]=3)[CH:42]=2)[CH:38]=[CH:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136409111tert-Butyl 4-[3-({4-methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-carbamoyl)-5-(pentafluoro-lambda6-sulphanyl)phenyl]piperazin-1-carboxylate

Product 1

HCID 136409110N-{4-Methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

210 mg (0.19 mmol, purity 61%) of the compound from Example 47A were stirred in 4.4 ml of a 25% strength solution of trifluoroacetic acid in methylene chloride at RT for 30 min. The mixture was then concentrated under reduced pressure. The residue was dissolved in a little methanol and added to semiconcentrated aqueous sodium bicarbonate solution. After 15 min of stirring at RT, 15 ml of ethyl acetate were added. The precipitate formed was filtered off, and the organic phase of the filtrate was separated off, washed with water, dried over sodium sulphate, filtered and concentrated. Drying of the residue under reduced pressure gave 41 mg (37% of theory) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a little methanol
  3. additionadded to semiconcentrated aqueous sodium bicarbonate solution
  4. addition15 ml of ethyl acetate were added
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. customthe organic phase of the filtrate was separated off
  8. washwashed with water
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customDrying of the residue under reduced pressure

Sources & evidence

ORD record
ord-89c74c610bef4dbaa8cd5e603a6fad34
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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