Water → N-cyclopropyl-4-methyl-3-(1-(2-methyl-3-oxopiperazin-1-yl)phthalazin-6-yl)benzamide

HRID 2357675Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH:13]1[CH3:19])=[N:7][N:6]=[CH:5]2.[CH:20]1([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[CH:20]1([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([N:12]3[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH:13]3[CH3:19])=[N:7][N:6]=[CH:5]4)[CH:26]=2)[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 90 °C

Procedure

This compound was prepared by a method analogous to that described in Example 8 (Method A). A mixture of 4-(6-bromophthalazin-1-yl)-3-methylpiperazin-2-one (0.200 g, 0.62 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.245 g, 0.81 mmol), sodium carbonate (0.270 g, 2.5 mmol) and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.040 g, 0.050 mmol) in DME (7 mL)/H2O (3 mL)/EtOH (2 mL) was heated at 90° C. The reaction was purified by flash chromatography eluting with 2M NH3 in MeOH/CH2Cl2 (0:1-1:19) to give 126 mg of a brown amorphous solid. The material was further purified by reverse phase HPLC (10→100% CH3CN [0.1% TFA]) to give the title compound as a light yellow amorphous solid. Found MS m/z: 416.2 [M+1].

Workup

customThis compound was prepared by a method analogous to
customThe reaction was purified by flash chromatography
washeluting with 2M NH3 in MeOH/CH2Cl2 (0:1-1:19)

Sources & evidence

ORD record: ord-59152d2db42844fa911d46de78872237
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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