Potassium Carbonate → N-cyclopropyl-4-methyl-3-(1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4, 3-a]pyrazin-7(8H)-yl)phthalazin-6-yl)benzamide

HRID 2357684Notes

Reaction equation

HRID 2357684 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH:25]1([NH:28][C:29](=[O:46])[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:31]=2)[CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:25]1([NH:28][C:29](=[O:46])[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([N:12]3[CH2:17][CH2:16][N:15]5[C:18]([C:21]([F:22])([F:24])[F:23])=[N:19][N:20]=[C:14]5[CH2:13]3)=[N:7][N:6]=[CH:5]4)[CH:31]=2)[CH2:26][CH2:27]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684535536-chloro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)phthalazine

Product 1

HCID 68455294N-cyclopropyl-4-methyl-3-(1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4, 3-a]pyrazin-7(8H)-yl)phthalazin-6-yl)benzamide

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the method described in Example 8 (Method A) using 6-chloro-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)phthalazine (350 mg, 987 μmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (594 mg, 1973 μmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (32 mg, 89 μmol), Pd2(dba)3 (27 mg, 30 μmol, Strem), and potassium carbonate (409 mg, 2960 μmol) in dioxane:H2O=4:1 (5 mL). Found MS (ES+) m/z: 494 (M+1).

Sources & evidence

ORD record
ord-6ec62f49a772418e93119b749da04e01
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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