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6-(2-acetylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In pyridine; dichloromethane; for 1.25h;
A solution of 170 mg (0.40 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3- trifluoromethyl-phenyl)-amide (Ex. 14) in 3 ml pyridine is diluted with 2 ml CH2CI2. Then 0.20 ml of an acetylchloride solution (2.2 M in CH2CI2; 0.44 mMol) are added dropwise, followed by another 0.10 ml after 40 min. After totally 75 min, the reaction mixture is diluted with EtOAc and H2O. The aqueous layer is separated off and extracted twice with EtOAc. The organic layers are washed with H2O and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 1 :1 ? EtOAc), partial concentration and crystallization by addition of DIPE gives the title compound: m.p.: 216-217 0C; MS: [M+1]+ = 467; TLC(EtOAc): R, = 0.36; HPLC: V/ = 13.1 ; Anal.: C1H1N1F.
With pyridine; In dichloromethane; for 1.25h;
Example 18: 6-(2-Acetylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3- trifluoromethyl-phenvD-annide; A solution of 170 mg (0.40 mMol) <strong>[861875-60-7]6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide</strong> (Ex. 14) in 3 ml pyridine is diluted with 2 ml CH2CI2. Then 0.20 ml of an acetylchloride solution (2.2 M in CH2CI2; 0.44 mMol) are added dropwise, followed by another 0.10 ml after 40 min. After totally 75 min, the reaction mixture is diluted with EtOAc and H2O. The aqueous layer is separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 1 :1 ? EtOAc), partial concentration and crystallization by addition of DIPE gives the title compound: m.p.: 216-217 0C; MS: [M+1]+ = 467; TLC(EtOAc): Rf = 0.36; HPLC: AtRe( = 13.1; Anal.: C1H1N1F.
6-(2-methoxycarbonylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In pyridine; dichloromethane; for 7.0h;
A solution of 200 mg (0.47 mMol) 6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3- trifluoromethyl-phenyl)-amide (Ex. 14) in 5 ml pyridine is diluted with 3 ml CH2CI2. Then 7.1 ml of a methyl chloroformate solution (2.8 M in CH2CI2; 20 mMol) are added portionwise during 7 h. The reaction mixture is diluted with EtOAc and H2O. The aqueous layer is separeted off and extracted twice with EtOAc. The organic layers are washed with H2O and brine, dried (Na2SO4) and concentrated. Stirring in DIPE gives the title compound: m.p.: 199- 200 0C; MS: [M+1]+ = 483; HPLC: %» = 13.6; Anal.: C1H1N1F.
With pyridine; In dichloromethane; for 7.0h;
Example 19: 6-(2-Methoxycarbonylamino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide; A solution of 200 mg (0.47 mMol) <strong>[861875-60-7]6-(2-amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide</strong> (Ex. 14) in 5 ml pyridine is diluted with 3 ml CH2CI2. Then 7.1 ml of a methyl chloroformate solution (2.8 M in CH2CI2; 20 mMol) are added portionwise during 7 h. The reaction mixture is diluted with EtOAc and H2O. The aqueous layer is separeted off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Stirring in DIPE gives the title compound: m.p.: 199-200 0C; MS: [M+1]+ = 483; HPLC: AtRe( = 13.6; Anal.: C1H1N1F.
6-(2-amino-6-chloro-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide[ No CAS ]
[ 861875-60-7 ]
Yield
Reaction Conditions
Operation in experiment
With hydrogen; triethylamine;palladium 10% on activated carbon; In tetrahydrofuran;
Example 14: 6-(2-Amino-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl- phenvD-amide; A solution of 660 mg (1.44 mMol) 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-naphthalene-1- carboxylic acid (3-trifluoromethyl-phenyl)-amide in 70 ml THF and 0.22 ml (1.58 mMol) Et3N is hydrogenated in the presence of 0.4 g Pd/C (10 %; Engelhard 4505). The catalyst is filtered off, the filtrate concentrated and the residue diluted with EtOAc and H2O. The aqueous layer is extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 1 :1 ? EtOAc) gives the title compound: m.p.: 218 0C; MS: [M+1]+ = 425; TLC(EtOAc/hexane 1 :1 ): Rf = 0.07.
With hydrogen; triethylamine;palladium 10% on activated carbon; In tetrahydrofuran;
A solution of 660 mg (1.44 mMol) 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide in 70 ml THF and 0.22 ml (1.58 mMol) Et3N is hydrogenated in the presence of 0.4 g Pd/C (10 %; Engelhard 4505). The catalyst is filtered off, the filtrate concentrated and the residue diluted with EtOAc and H2O. The aqueous layer is extracted twice with EtOAc. The organic layers are washed with H2O and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 1 :1 - > EtOAc) gives the title compound: m.p.: 218 0C; MS: [M+1]+ = 425; TLC(EtOAc/hexane 1 :1): R, = 0.07.
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