3-Methyl-1-(1-methylethyl)-1H-pyrazol-5-amine

General procedure: In a 1 dram vial, to a stirred solution of bicyclo[2.2.1]heptan-2-amine (15.0 mg, 0.13 mmol), 2-(5-phenyl-2H-tetrazol-2-yl)acetic acid (27.0 mg, 0.13 mmol) and TEA (54.8 muL, 0.40 mmol) in DCM (1 mL) was dropwise added propylphosphonic anhydride solution '50 wt. percent in ethyl acetate (107.4 muL, 0.16 mmol). The reaction was stirred at RT for 1 hour. The product was partitioned between ethyl acetate (15 mL * 2) and water (15 mL). Organic layers were combined, washed with brine, dried over sodium sulphate, concentrated and purified by reverse phase preparative chromatography (0-100percent ACN in water). (28.0 mg, 70percent)Intermediate 33Ethyl 6-cyclopropyl-3-methyl-l-(l-methylethyl)-lH-pyrazolo[3, 4-6]pyridine-4- carbox lateA solution of ethyl 4-cyclopropyl-2, 4-dioxobutanoate (700 mg, 3.76 mmol), 3- methyl-l-(l-methylethyl)-lH-pyrazol-5 -amine (523 mg, 3.76 mmol) and benzene (20 mL) were heated at 65 °C for 6 hr, and then allowed to cool to room temperature for 2 d. The solvent was removed under reduced pressure and the residue purified via silica gel chromatography (eluent: 0 to 25percent EtOAc:Hex). The final product was collected as 0.77 g (71percent). LCMS E-S (M+H) = 288.0. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.04 - 1.11 (m, 2 H), 1.13 - 1.20 (m, 4 H), 1.47 (t, J=7.20 Hz, 6 H), 1.55 (d, J=6.82 Hz, 12 H), 2.16 - 2.25 (m, 2 H), 2.68 (s, 6 H), 4.49 (q, J=7.07 Hz, 4 H), 5.20 (spt, J=6.78 Hz, 2 H), 7.41 (s, 1 H).Intermediate 33Ethyl 6-cyclopropyl-3-methyl-l-(l-methylethyl)-lH-pyrazolo[3, 4-6]pyridine-4- carbox lateA solution of ethyl 4-cyclopropyl-2, 4-dioxobutanoate (700 mg, 3.76 mmol), 3- methyl-l-(l-methylethyl)-lH-pyrazol-5 -amine (523 mg, 3.76 mmol) and benzene (20 mL) were heated at 65 °C for 6 hr, and then allowed to cool to room temperature for 2 d. The solvent was removed under reduced pressure and the residue purified via silica gel chromatography (eluent: 0 to 25percent EtOAc:Hex). The final product was collected as 0.77 g (71percent). LCMS E-S (M+H) = 288.0. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.04 - 1.11 (m, 2 H), 1.13 - 1.20 (m, 4 H), 1.47 (t, J=7.20 Hz, 6 H), 1.55 (d, J=6.82 Hz, 12 H), 2.16 - 2.25 (m, 2 H), 2.68 (s, 6 H), 4.49 (q, J=7.07 Hz, 4 H), 5.20 (spt, J=6.78 Hz, 2 H), 7.41 (s, 1 H).

Molecular Weight:139.20
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:139.110947427
Monoisotopic Mass:139.110947427
Topological Polar Surface Area:43.8
Heavy Atom Count:10
Complexity:113
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes