HCID 59242666, compound → HCID 24880031, compound

HRID 1485864Notes

Reaction equation

HRID 1485864 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:26]([F:29])([F:28])[F:27])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[C:20]1([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:26]([F:29])([F:28])[F:27])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 59242666HCID 59242666, compound

Product 1

HCID 24880031HCID 24880031, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(5-phenyl-6-trifluoromethyl-pyridazin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (D4) (1.8 g, 0.0044 mol) in methanol (125 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (5.3 g, 0.022 mol) 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 crystallised from ether/heptane to yield E1 (1.3 g, 96%). C15H15F3N4 requires 308; Found 309 (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 crystallised from ether/heptane

Sources & evidence

ORD record
ord-da4f7f62e21c40ea9557d25347d0d644
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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