HCID 59242670, compound → HCID 59242651, compound

HRID 1485874Notes

Reaction equation

HRID 1485874 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[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>CO>[Cl:25][C:22]1[S:21][C:20]([C:18]2[CH:19]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=[N:16][C:17]=2[C:26]([F:29])([F:27])[F:28])=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 59242670HCID 59242670, compound

Product 1

HCID 59242651HCID 59242651, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[5-(5-chloro-thiophen-2-yl)-6-trifluoromethyl-pyridazin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (D15) (0.114 g, 0.25 mmol) in methanol (10 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (0.305 g, 1.25 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 then purified by column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The crude product was dissolved in a 2 M solution of hydrochoric acid in diethyl ether and the mixture stirred at room temperature for 16. The solvent was evaporated in vacuo. The solid obtained was triturated from diethyl ether to yield E27 (0.062 g, 87%). C13H12ClF3N4S requires 348; Found 349 (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 then purified by column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo
  10. dissolutionThe crude product was dissolved in a 2 M solution of hydrochoric acid in diethyl ether
  11. stirringthe mixture stirred at room temperature for 16
  12. customThe solvent was evaporated in vacuo
  13. customThe solid obtained
  14. customwas triturated from diethyl ether
  15. customto yield E27 (0.062 g, 87%)

Sources & evidence

ORD record
ord-f32c5ef934484969b864ed950d1e88d6
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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