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8-amino-2-(2-chloro-4-fluorophenyl)-2-azaspiro[4.5]decan-1-one[ No CAS ]
N-[(trans)-2-(2-chloro-4-fluorophenyl)-1-oxo-2-azaspiro[4.5]dec-8-yl]pyrazolo[1,5-a]pyrimidine-2-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; for 16.0h;
To 8-amino-2-(2-chloro-4-fluorophenyl)-2-azaspiro[4.5]decan-1 -one (isomer 1 ) (44.5 mg, 150 muiotaetaomicronIota, Intermediate 112), in NMP (1 .0 ml) was added pyrazolo[1 ,5-a]pyrimidine-2-carboxylic acid (31 .8 mg, 195 mupiiotaomicronIota) in NMP (0.34 ml). HATU (74.1 mg) in NMP (0.5 ml) and N,N- diisopropylethylamine (50.4 mg, 0.390 mmol) in NMP (0.5 ml) were added. The resulting mixture was shaked for 16 h. The reaction mixture was filtered and the filtrate containing the crude product was subjected to preparative HPLC purification to give the title compound (13.4 mg, 18% yield).LC-MS (Method 5): Rt= 1 .02 min; MS (ESIpos): m/z = 442 [M+H]+
trans-4-amino-N-(2-chloro-4-fluorophenyl)cyclohexanecarboxamide hydrochloric acid salt[ No CAS ]
N-{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}pyrazolo[1,5-a]pyrimidine-2-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
9%
With N-ethyl-N,N-diisopropylamine; HATU; In 1-methyl-pyrrolidin-2-one; for 16.0h;
To trans-4-amino-N-(2-chloro-4-fluorophenyl)cyclohexanecarboxamide hydrochloric acid salt (40.6 mg, 150 muiotaetaomicronIota, Intermediate I2) in NMP (1.0 ml) was added pyrazolo[1 ,5-a]pyrimidine-2- carboxylic acid (31 .8 mg, 195 muiotaetaomicronIota) in NMP (0.35 ml). HATU (74.1 mg) in NMP (0.5 ml) and N,N-diisopropylethylamine (50.4 mg, 0.390 mmol) in NMP (0.5 ml) were added. The resulting mixture was shaked for 16 h. The reaction mixture was filtered and the filtrate containing the crude product was subjected to preparative HPLC purification to give the title compound (6.2 mg, 9% yield). (0541) LC-MS (Method 5): Rt = 0.98 min; MS (ESIpos): m/z = 416 [M+H]+