Trifluoroacetic acid → HCID 59242667, compound

HRID 1485872Notes

Reaction equation

HRID 1485872 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:33]([F:36])([F:35])[F:34])=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18]3[CH:19]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[N:15]=[N:16][C:17]=3[C:33]([F:36])([F:34])[F:35])=[CH:25][CH:24]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59242652HCID 59242652, compound

Product 1

HCID 59242667HCID 59242667, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[5-(4′-fluorobiphenyl-4-yl)-6-trifluoromethyl-pyridazin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (D12) (0.115 g, 0.23 mmol) and trifluoroacetic acid (2 ml) in dichloromethane (8 ml) was stirred at room temperature for 2 h. The solvent was evaporated in vacuo and then, dichloromethane and a saturated solution of sodium carbonate were added. The organic layers were separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was then purified by column chromatography (silica gel; 1-3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo to yield E9 (0.084 g, 91%). C21H18F4N4 requires 402; Found 403 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additiondichloromethane and a saturated solution of sodium carbonate were added
  3. customThe organic layers were separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue was then purified by column chromatography (silica gel; 1-3% ammonia in methanol (7M)/dichloromethane)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0e21dc9bf9e4e4a8e4c2014b146ce82
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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