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

HRID 324345Notes

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-dbf252ddb29a43fe991dea3db9392415
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218392B1

Reaction notes

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