5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile → HCID 127045542, compound
Reaction equation
CC(=O)Nc1cc(N)ccc1N1CCC[C@@H](N(C)C)C1.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)ccc1N1CCC[C@@H](N(C)C)C1Participants
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 (120mg, 0.51 mmol), (R)-N-(5-amino-2-(3-(dimethylamino)piperidin-1-yl)phenyl)acetamide (142 mg, 0.51 mmol), and cesium carbonate (335 mg, 1.03 mmol) in DMA (0.5 mL) (),Pd2(dba)3 (23.51 mg, 0.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.7 mg, 0.05 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added MeOH (2 mL), filtered. The solvent was removed by ratovapor to yield stick oil. The crude product was loaded on ISCO (Hex to Hex:EtOAc To EtOAc to EtOAc:MeOH:Et3N=10:1:0.1) to give sticky oil. The product was not pure. It was purifed by to give (R)-N-(5-(3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-(3-(dimethylamino)piperidin-1-yl)phenyl)acetamide (22.00 mg, 7.29 %) as a light brown solid (TFA salt). the solid was dried under high vacuum under 60C for 2h. LCMS and NMR were OK, see the attachment
Sources & evidence
- ORD record
- ord-6a2cb6eee4e6411fbe36a812955f2574
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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