Ethyl Acetate → Yze9gcm2BB

HRID 47333Notes

Reaction equation

HRID 47333 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[C:5]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)=[N:4][N:3]=1.[OH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O>[OH:25][CH:26]1[CH2:31][CH2:30][N:29]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=3)[C:5]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=3)=[N:4][N:3]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrile

Product 1

HCID 9888568Yze9gcm2BBYield 85.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

10.0 g of 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine was dissolved in 50 ml 1-methyl-2-pyrrolidone, then 43.32 g of 4-hydroxypiperidine and 10 ml diisopropylethylamine were added thereto, and the mixture was heated at 170° C. for 8 hr. After cooling, ethyl acetate was added thereto, and the mixture was washed 3 times with water and once with brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to give 10.1 g of 1-(4-hydroxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine as yellow crystals.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed 3 times with water
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3c9d8bdbc7904fc7bd47f8bbdab1c318
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

Loading…