Ethyl Acetate → Yze9gcm2BB

HRID 1595175Notes

Reaction equation

HRID 1595175 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>CN1CCCCC1=O>[Cl:24][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[O:22][CH3:23])[CH2:15][NH:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=2)[C:2]([N:29]2[CH2:30][CH2:31][CH:26]([OH:25])[CH2:27][CH2:28]2)=[N:3][N:4]=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 13603N-Methyl-2-piperidoneSolvent

Conditions

Temperature
170 °C

Procedure

1H-NMR(400 MHz, CDCl3) δ: 3.87(3H, s), 4.78(2H, d, J=5.0 Hz), 5.75(1H, t, J=5.0 Hz), 6.87(1H, d, J=8.5 Hz), 7.31(1H, dd, J=8.5, 2.0 Hz), 7.43(1H, d, J=2.0 Hz), 8.05(1H, dd, J=8.5, 1.5 Hz), 8.24(1H, dd, J=1.5, 1.0 Hz), 8.29(1H, dd, J=8.5, 0.5 Hz). 10.0 g of 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine was dissolved in 50 ml of N-methyl-2-piperidone. After adding 43.32 g of 4-hydroxypiperidine and 10 ml of diisopropylethylamine, the resulting mixture was heated at 170° C. for 8 hours. Then ethyl acetate wag added thereto and the resulting mixture was successively washed for three times with water and once with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1) to give 10.1 g of 4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-hydroxypiperidino)phthalazine as yellow crystals. M.p.: 172.0-173.5° C., Mass 424(MH+),

Workup

  1. washthe resulting mixture was successively washed for three times with water and once with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter evaporating the solvent
  4. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-57f29baa2f6f414b8445dcefad9aa072
Source dataset
uspto-grants-2001_09
Patent number
US06288064B1

Reaction notes

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