HCID 59242665, compound → HCID 59242661, compound

HRID 1485869Notes

Reaction equation

HRID 1485869 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][C:23]([F:26])=[CH:22][CH:21]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[CH:19]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[N:15]=[N:16][C:17]=2[C:27]([F:30])([F:28])[F:29])=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 59242665HCID 59242665, compound

Product 1

HCID 59242661HCID 59242661, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[5-(4-fluorophenyl)-6-trifluoromethyl-pyridazin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (D8) (1.25 g, 2.93 mmol) in methanol (50 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (3.6 g, 14.64 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 crude product was purified by HPLC. The desired fractions were collected and evaporated in vacuo to yield E6 (0.507 g, 53%). C15H14F4N4 requires 326; Found 327 (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 crude product was purified by HPLC
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5bfa1423a2fe41d9bb3a300c9e1fcd66
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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