3-AMINO-4-PYRIDINECARBOXAMIDE

Ammonium hydrochloride (4.98 g, 93.2 mmol) was added to 3-aminoisonicotinic acid (9.90g, 71.7 mmol), 2-(3H-[1, 2, 3]triazolo[4, 5-b]pyridin-3-yl)-1, 1, 3, 3-tetramethylisouronium hexafluorophosphate(V) (35.4 g, 93.2 mmol) and N-ethyl-N-isopropylpropan-2-amine (37.5mL, 215.02 mmol) in DMF (100 mL) under nitrogen. The resulting solution was stirred at 40 °C for 72 hours. The mixture was evaporated to provide the crude material. The crude product was purified by flash silica chromatography with elution gradient 5percent MeOH in DCM. Pure fractions were evaporated to dryness to afford 3-aminoisonicotinamide (8.57 g, 87 percent) as a yellow gum.To the suspension of isonicotinic acid (1.00 g, 7.24 mmol) in DMF (10 mL) were added HOBt (978 mg, 7.24 mmol), 7 M ammonia solution in methanol (2.06 mL, 14.5 mmol) and EDC*HCl (2.08 g, 10.9 mmol). The mixture was stirred overnight at room temperature. Solvent was distilled off in vacuo, and CH (1.70 g, 12.40 mmol) was added to c.HCl (20 mL, 12.40 mmol) at ambient temperature. 35% hydrogen peroxide in water (1.17 mL, 13.64 mmol) was added dropwise to the reaction mixture under an atmosphere of nitrogen. The resulting solution was stirred for 1 hour. The mixture was neutralised with NaOH solution and extracted into EtOAc (150 mL). The organic layer was dried over MgSO4, filtered and concentrated to afford the crude product which was purified by flash silica chromatography with EtOAc as eluent. Pure fractions were evaporated to dryness to afford 3-amino-2-chloroisonicotinamide (0.58 g, 27%) as a yellow solid.General procedure: 1800 muL (90%) Tris buffer (50 mM, pH 7.6) and 200 muL(10%) of methanol or acetone. In a 2 mL Eppendorf, NHase (10 mg) was added followed by Trisbuffer. Nitrile substrate (10 mg dissolved in 200 muL methanol or acetone) was added to the 2 mLEppendorf tube. (If an amine group was present on the nitrile substrate a Tris buffer of pH 9 wasused). The reaction mixture was incubated at 30 C on an ESCO Provocell microplateshaker/incubator (Esco Technologies, Halfway House, South Africa) (199 rpm). The reaction wasallowed to proceed for 24 h, 48 h or 5 d, depending on conversion, as monitored by TLC analysis.Ethyl acetate and water were added to the reaction mixture, and after separation, the organic layerwas concentrated under reduced pressure, and the resulting mixture was then purified by silica gelcolumn chromatography eluting with 20% to 90% ethyl acetate/ hexane.In a 20 mL microwave vial was added In a two necked R.B. flask fitted with thermometer pocket and nitrogen inlet, TBTU (4.75 g, 14.8 mmol) and N, /V-diisopropylethylamine (2.6 mL, 14.8 mmol) were added to a stirred solution of In a two necked R.B. flask fitted with thermometer pocket and nitrogen inlet, TBTU (4.75 g, 14.8 mmol) and N, /V-diisopropylethylamine (2.6 mL, 14.8 mmol) were added to a stirred solution of

Molecular Weight:137.14
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.058911855
Monoisotopic Mass:137.058911855
Topological Polar Surface Area:82
Heavy Atom Count:10
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes