HCID 59242659, compound → HCID 59242650, compound

HRID 1485873Notes

Reaction equation

HRID 1485873 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:26]#[N: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[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=[N:16][C:17]=2[C:26]#[N:27])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 59242659HCID 59242659, compound

Product 1

HCID 59242650HCID 59242650, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(6-cyano-5-phenyl-pyridazin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (D14) (0.133 g, 0.37 mmol) in methanol (10 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (1.3 g, 5.3 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. The desired fractions were collected and evaporated in vacuo to yield EN (0.06989 g, 72%) as a white solid. C15H15N5 requires 265; Found 266 (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
  10. customto yield EN (0.06989 g, 72%) as a white solid

Sources & evidence

ORD record
ord-a2d7e76780524c49bb7ae6cbd6c51a0a
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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