HCID 59242664, compound → HCID 59242654, compound

HRID 1630477Notes

Reaction equation

HRID 1630477 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:27]([F:30])([F:29])[F:28])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[N:11]1([C:14]2[N:15]=[N:16][C:17]([C:27]([F:29])([F:28])[F:30])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 59242664HCID 59242664, compound

Product 1

HCID 59242654HCID 59242654, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[5-(2-tolyl)-6-trifluoromethyl-pyridazin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (D11) (0.089 g, 0.21 mmol) in methanol (7 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (0.257 g, 1.05 mmol) and the reaction mixture was shaken at room temperature for 18 h. After this period, the mixture was filtered and then a saturated solution of ammonia in methanol was added. The mixture was shaken for 1 h, filtered and the filtrate evaporated in vacuo. The residue was purified by HPLC and the desired fractions were collected and evaporated in vacuo to yield E8 (0.026 g, 50%) as a white solid. C16H17F3N4 requires 322; Found 323 (MH+).

Workup

  1. waitAfter this period
  2. filtrationthe mixture was filtered
  3. additiona saturated solution of ammonia in methanol was added
  4. stirringThe mixture was shaken for 1 h
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe residue was purified by HPLC
  8. customthe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-9b73c9e697c148b9868f043f8fe56ee2
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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