CO[CH2:3][NH2:4].[C:5]([O-])([O-])=[O:6].[K+].[K+].ClC1C=C(SC[C:20]2[C:21]([C:26]([OH:28])=O)=[N:22][CH:23]=[CH:24][CH:25]=2)C=CC=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1.O.C1COCC1.O.CN(C=O)C>[CH3:5][O:6][N:4]([CH3:3])[C:26]([C:21]1[CH:20]=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:28]
N-Methoxymethylamine (1.05 g) was dissolved in THF-water (25:1, 5 ml) with anhydrous K2CO3 (1.5 g), and the solution was stirred at room temperature for 30 minutes. It was then transferred by syringe into a flask containing 3-[(3-chlorophenyl)thiomethyl]-2-pyridinecarboxylic acid (2.0 g, 7.16 mmol) in a mixture of THF (3 ml), DMF (2 ml) and NMM (0.5 ml). HOBT (180 mg, 1.33 mmol) and EDCI (255 mg, 1.33 mmol) were added at 0° C. and the mixture was then stirred 28 hours at room temperature. The reaction mixture was diluted with water and extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The product was chromatographed on silica in 2%MeOH/CH2Cl2 and afforded 200 mg of 3-[(3-chlorophenyl)thiomethyl)]-N-methoxy-N-methyl-2-pyridinecarboxamide; MS (EI, M)=292; MS (CI, M+H)=293.
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