Reaction equation
CC(=O)Nc1cc(N)c(F)cc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>CC(=O)N(C)C.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.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(NC3COC3)n3ncc(C#N)c3n2)c(F)cc1C1CC1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 145 °C
Procedure
In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (0.167 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08 mmol). anhydrous DMA (1.0 mL) was added. The resulting mixture was bubbled through N2. Then the tube was capped. under microwave 145C for 25min. LCMS showed product and byproduct mass, did not showed SM The mixture was filtered through celite. The resulting black solution was concentrated to dryness by rotavapor. The crude product was purified by ISCO (40g, Hex to EtOAc:HEx=1;2 to 1;1 to EtOAcO) to give product (offwhite solid). HPLC showed some impurity. This offwhite solid was washed with warm EtOAc (1mL) to giveN-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropyl-4-fluorophenyl)acetamide (0.012 g, 3.55 %) LCMS and NMR were OK, see attachment.
Sources & evidence
- ORD record
- ord-bfef1bef76ff43f7a429af888b0d1628
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
Loading…