Potassium Carbonate → HCID 68453228, compound

HRID 2357678Notes

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](=[O:21])[O:19][CH2:20][C@@H:14]3[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH:22]1([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1>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].O1CCOCC1>[O:21]=[C:18]1[N:15]2[CH2:16][CH2:17][N:12]([C:8]3[C:9]4[C:4](=[CH:3][C:2]([C:29]5[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=5[CH3:33])[C:26]([NH:25][CH:22]5[CH2:23][CH2:24]5)=[O:43])=[CH:11][CH:10]=4)[CH:5]=[N:6][N:7]=3)[CH2:13][C@H:14]2[CH2:20][O:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (S)-7-(6-chlorophthalazin-1-yl)-tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one (0.600 g, 1.97 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1.110 g, 3.69 mmol), potassium carbonate (0.875 g, 6.33 mmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (0.136 g, 0.373 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.107 g, 0.117 mmol) in 12 mL of degassed 80% aqueous 1,4-dioxane was heated at 80° C. The crude material was purified flash chromatography eluting with 2 M NH3 in MeOH/CH2Cl2 (0:1→3:97) to give 1.26 g of an orange liquid. The material was further purified by reverse-phase HPLC (Phenomenex Synergi 4u MAX-RP 80, 150×21.2 mM) eluting with 0.1% formic acid-CH3CN:0.1% formic acid-H2O (1:9→9:1) to give the title compound as a white amorphous solid.

Workup

customThe crude material was purified flash chromatography
washeluting with 2 M NH3 in MeOH/CH2Cl2 (0:1→3:97)

Sources & evidence

ORD record: ord-9b612f0d0e494834bb03beab5c3871b3
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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