N-methyl-2-morpholin-4-ylacetamide → N-methyl-2-morpholin-4-yl-N-[6-(2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-2-yl]acetamide

HRID 200Notes

Reaction equation

HRID 200 reaction equation
CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1

Participants

7

Reactant 2

HCID 22031405N-methyl-2-morpholin-4-ylacetamideHCID 87563685[6-(2-Morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-2-yl] trifluoromethanesulfonate

Product 1

HCID 68758915N-methyl-2-morpholin-4-yl-N-[6-(2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-2-yl]acetamideYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (100mg, 0.18 mmol) in dry dioxane (1 ml) was added to a stirred mixture of N-methyl-2-morpholinoacetamide (33.8 mg, 0.21 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.08 mg, 4.45 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.15 mg, 8.90 µmol) and cesium carbonate (232 mg, 0.71 mmol) in dry dioxane (1 ml) . The resulting mixture was stirred under nitrogen at 110 °C for 3 hours. UPLC analysis showed no appreciable product only hydrolysis of the triflate - not isolated , reaction abandonned

Sources & evidence

ORD record
ord-26b0abcb83694e11aba5d8cb57edf605
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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