Water → 1-(4-Tert-butoxycarbonyl-piperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine

HRID 1457545Notes

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.[NH:25]1[CH2:37][CH2:36][CH:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:26]1.O>CN1CCCC1=O>[C:32]([O:31][C:29]([CH:28]1[CH2:36][CH2:37][N:25]([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)[CH2:26][CH2:27]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

Conditions

Temperature: 170 °C

Procedure

1-Chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine (2 g) prepared in Example 1 and t-butyl isonipecotate (2 g) were dissolved in 20 ml of N-methyl-2-pyrrolidone. The obtained solution was heated at 170° C. for 5 hours and cooled, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The obtained residue was subjected to silica gel column chromatography and eluted with toluene/tetrahydrofuran (10:1) to give 1.6 g of 1-(4-tert-butoxycarbonyl-piperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine.

Workup

temperaturecooled
extractionThe obtained mixture was extracted with ethyl acetate
washThe organic phase was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in a vacuum
washeluted with toluene/tetrahydrofuran (10:1)

Sources & evidence

ORD record: ord-6d9c90cca1e04140b2a4c202134afedd
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849741

Reaction notes

Loading…