4-(Trifluoromethyl)benzaldehyde → HCID 59253662, compound

HRID 1258153Notes

Reaction equation

HRID 1258153 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[N:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8]3[N:13]=[N:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59253661HCID 59253661, compound

Product 1

HCID 59253662HCID 59253662, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-(piperidin-4-ylamino)-pyridazine-3-carbonitrile (D3) (0.15 g, 0.7 mmol) and α,α,α-trifluoro-p-tolualdehyde (0.15 ml, 1.1 mmol) in dichloromethane (2 ml), was added sodium triacetoxyborohydride (0.232 g, 1.1 mmol) and acetic acid (0.041 ml). The reaction mixture was then stirred at room temperature for 18 h. A saturated solution of sodium hydrogen carbonate was then added and the organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by HPLC. The desired fractions were collected and the solvent was evaporated in vacuo to yield E7 (0.101 g, 38%) as a solid. C18H18F3N5 requires 361. Found 362 (MH+); mp: 243.1° C.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by HPLC
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-68f03510272b4d7c8d032d30853a599b
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

Loading…