5-Chloro-N-methyl-2-pyridinamine

Off-White Solid

General procedure: Copper (II) acetate (0.550 g, 3.03 mmol) was added to a solution of aniline (1.22 mmol) and pyridine (0.34 mL, 4.24 mmol) in dioxane (15 mL). The mixture was stirred for 15 min, methyl boronic acid (0.181 g, 3.03 mmol) was added, and the reaction was refluxed until aniline was totally consumed (TLC analysis, 1.5- 18 h). The reaction mixture was allowed to reach room temp, filtered through Celite, and the solvent was evaporated. The residue was purified by flash chromatography (0→50percent EtOAc/hexanes) to afford N-methylaniline. [0233] 5-chloro-N-methylpyridin-2-amine (162). Compound 162 was prepared according to procedure F from 160 to afford 73 mg of brown powder (42percent). 1H NMR (500 MHz, CDC1General procedure: A solution of 3-amino-6-chloropyridine (2.46 g, 19.2 mmol) in THF (50 mL) was added to a suspension of NaH (60% dispersion in mineral oil, 768 mg, 19.2 mmol) and THF (150 mL). The reaction stirred at room temperature for 3 hours, lodomethane (1.2 mL, 19.2 mmol) was added and the reaction was heated to 40 C for 9 hours. After cooling to room temperature, the solvent was removed. The crude material was tritrated in dichloromethane (100 mL) and filtered to remove any salts. The filtrate was purified by flash chromatography (silica, 10-80% ethyl acetate/hexanes). 1H NMR (400 MHz, CDCI3) 5 7.72 (d, J= 3.1, 1H), 7.06 (d, J= 8.6, 1H), 6.83 (dd, J= 3.1, 8.6, 1H), 3.78 (s, 1H), 2.84 (d, J= 19.7, 3H).General procedure: Copper (II) acetate (0.550 g, 3.03 mmol) was added to a solution of aniline (1.22 mmol) and pyridine (0.34 mL, 4.24 mmol) in dioxane (15 mL). The mixture was stirred for 15 min, methyl boronic acid (0.181 g, 3.03 mmol) was added, and the reaction was refluxed until aniline was totally consumed (TLC analysis, 1.5- 18 h). The reaction mixture was allowed to reach room temp, filtered through Celite, and the solvent was evaporated. The residue was purified by flash chromatography (0'50% EtOAc/hexanes) to afford N-methylaniline. [0233] 5-chloro-N-methylpyridin-2-amine (162). Compound 162 was prepared according to procedure F from 160 to afford 73 mg of brown powder (42%). 1H NMR (500 MHz, CDC13) delta 2.90 (s, 3H), 4.79 (brs, 1H), 6.33 (d, J = 8.9Hz, 1H), 7.38 (dd, J = 2.6, 8.9Hz, 1H), 8.02 (d, J = 2.6Hz, 1H). 13C NMR (126 MHz, CDC13) delta 29.22, 106.90, 119.44, 137.27, 146.26, 157.88. LCQ (M+H+) calcd C6H7C1N2 143, found 143.General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2×) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.To s suspension of sodium hydride (60% dispersion in mineral oil, 46 mg, 1.1 mmol) in terahydorofuran (4 ml) was added REFERENTIAL EXAMPLE 390 Methyl 2-[(5-chloropyridin-2-yl)(methyl)amino]-2-oxoacetate: The title compound was obtained from Compound AQ A mixture of Compound AR A stirred mixture of

5-Chloro-2-methylaminopyridine is used in the preparation of aminosulfuranes with N-heterocyclic groups.

Molecular Weight:142.58
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:142.0297759
Monoisotopic Mass:142.0297759
Topological Polar Surface Area:24.9
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes