5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile → HCID 127045536, compound
Reaction equation
CC(=O)Nc1cc(N)ccc1N(C)CCCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>CC(=O)N(C)C.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]>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCCN(C)CParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 150 °C
Procedure
In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (70mg, 0.30 mmol), N-(5-amino-2-((3-(dimethylamino)propyl)(methyl)amino)phenyl)acetamide (79 mg, 0.30 mmol), and cesium carbonate (195 mg, 0.60 mmol) in DMA (0.5 mL) (),Pd2(dba)3 (13.72 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.33 mg, 0.03 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS comletion. MeOH (2 mL) was added to the reaction mixture. filtered. The mother liquid solvent was removed by ratovapor to yield sticky oil. The crude product was loaded on ISCO (Hex to Hex:EtOAc To EtOAc to EtOAc:MeOH=10:1) to give sticky oil. The product was not pure. It was purified by to give N-(5-(3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-((3-(dimethylamino)propyl)(methyl)amino)phenyl)acetamide (50.0 mg, 29.0 %) as TFA salt NMR and LCMS showed desired product, see attachment.
Sources & evidence
- ORD record
- ord-f3666d844cbc446dba498aa63de90f9a
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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