6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → gamma-Secretase modulator 6

HRID 344

Reaction equation

HRID 344 reaction equation
CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.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]>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1cnn(C)c1

Participants

6

Reactant 2

HCID 575128666-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamineHCID 57512880(2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine

Product 1

HCID 49819500gamma-Secretase modulator 6Yield 0%

Reagents, catalysts & solvents 3

HCID 10796Cesium carbonateReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

Charged a standard microwave vial with a mixture of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (100 mg, 0.49 mmol), (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (135 mg, 0.49 mmol), cesium carbonate (239 mg, 0.73 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.42 mg, 0.02 mmol), Tri-tert- butylphosphonium tetrafluoroborate (14.21 mg, 0.05 mmol), and 1,2-dimethoxyethane. The atmosphere was inerted through vacuum-nitrogen cycles and the contents were heated at 120 °C for a period of 30 min. LCMS indicates reaction progression is less than 10%. Reaction aborted. Not progressed.

Sources & evidence

ORD record
ord-f55732d796df4a6bad136ec929c58223
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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