1,3-DIMETHYL-1H-PYRAZOL-4-AMINE

General procedure: To a solution of 5 (0.56mmol) and corresponding aromatic amine in DMF (10mL) was added Cs2CO3 (511mg, 1.57mmol) under N2 protection. Pd2(dpa)3(33mg, 0.036mmol) and BINAP (67mg, 0.108mmol) were added, and the resulting reaction was stirred 90C. After 7h, the mixture was cooled to room temperature, diluted with water (30mL), and extracted with ethyl acetate (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 8-100% ethyl acetate in CH2Cl2 to provide the desired product.General procedure: To a solution of 5 (0.56mmol) and corresponding aromatic amine in DMF (10mL) was added Cs2CO3 (511mg, 1.57mmol) under N2 protection. Pd2(dpa)3(33mg, 0.036mmol) and BINAP (67mg, 0.108mmol) were added, and the resulting reaction was stirred 90C. After 7h, the mixture was cooled to room temperature, diluted with water (30mL), and extracted with ethyl acetate (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 8-100% ethyl acetate in CH2Cl2 to provide the desired product.General procedure: To a solution of 5 (0.56mmol) and corresponding aromatic amine in DMF (10mL) was added Cs2CO3 (511mg, 1.57mmol) under N2 protection. Pd2(dpa)3(33mg, 0.036mmol) and BINAP (67mg, 0.108mmol) were added, and the resulting reaction was stirred 90C. After 7h, the mixture was cooled to room temperature, diluted with water (30mL), and extracted with ethyl acetate (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 8-100% ethyl acetate in CH2Cl2 to provide the desired product.General procedure: To a solution of 9 (0.50mmol) and corresponding aromatic amine (0.55mmol) in DMF (10mL) was added Cs2CO3 (455mg, 1.40mmol) under N2 protection. Pd2(dpa)3(30mg, 0.033mmol) and BINAP (62mg, 0.10mmol) were added, and the resulting reaction was stirred 90C. After 7h, the mixture was cooled to room temperature, diluted with water (30mL), and extracted with ethyl acetate (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 8-100% ethyl acetate in CH2Cl2 to provide the desired product. 4.1.8.1 (R)-1-(2-((1, 3-dimethyl-1H-pyrazol-4-yl)amino)pyridin-4-yl)-N-(4-(trifluoromethoxy)benzyl)piperidine-3-carboxamide (3a) (0050) Compound 9 (225mg, 0.50mmol) was reacted with General procedure: A mixture of compound 7a (212 mg, 0.50 mmol), 1-methyl-1H-pyrazol-4-amine (97 mg, 1.00 mmol), Pd2 (dpa)3 (30 mg, 0.03 mmol), BINAP (60 mg, 0.10 mmol) and Cs2CO3 (446 mg, 1.40 mmol) in DMF (15 mL) was degassed and charged with nitrogen for three times and then heated in an oil bath at 90 C for 7 h under the protection of nitrogen. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (30 mL * 3). The combined organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The concentrates was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2 (8%-100%) to give 8a (90 mg, 45%).

Molecular Weight:111.15
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:111.079647300
Monoisotopic Mass:111.079647300
Topological Polar Surface Area:43.8
Heavy Atom Count:8
Complexity:83.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes