1,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylate

A suspension of 10percent Pd-C (0.054 g, 0.051 mmol in Pd) and the above carbamate Example 105 (2.647 g, 10.1 mmol) in 95percent EtOH was degassed under reduced pressure then reacted under hydrogen. After 23 h the solvent was evaporated on a rotary evaporator. EtOAc (20 mL) was added and the reaction filtered then slowly EPO A soln of di-tert-butyl dicarbonate (6.719 g, 30.8 mmol) in DCM (20 mL) was added over 5 min to a suspension of 5-nitro-lH-indazole (5.009 g, 30.7 mmol), EtCompound TDI01234-1 (2.0 g, 8.86 mmol) was dissolved in 1, 2-dichloroethane (150 mL), triethylamine (746 mg, 7.38 mmol) was added, and the reaction solution was warmed to 30°C and stirred for 1.5 hours. Tert-butyl 5-amino-1H-indazole-1-carboxylate (1.72 g, 7.38 mmol) and acetic acid (443 mg, 7.38 mmol) were then added, after stir of 0.5 hour, sodium triacetoxyborohydride (4.69 g, 22.14 mmol) was added, and the reaction was maintained at 30°C overnight. Thin layer chromatography (dichloromethane : methanol =60:1) assay indicated the reaction was complete. The reaction solution was dissolved in dichloromethane (1500 ml), successively washed with water (150 ml * 2) and saturated brine (150 ml), and the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (dichloromethane : methanol = 1:0 to 60:1), to afford compound TDI01234-2 (1.0 g, brown yellow solid). 1H NMR (400 MHz, CDCl3) delta 7.96 (s, 1H), 7.93 (d, J = 8.8 Hz, 1H), 7.30 (dd, J= 13.6, 5.2 Hz, 4H), 7.24 (dd, J = 5.2, 3.2 Hz, 1H), 6.88 (dd, J= 8.8, 2.1 Hz, 1H), 6.75 (d, J= 1.6 Hz, 1H), 4.16 (s, 1H), 3.66 - 3.44 (m, 3H), 2.57 (d, J = 120.0 Hz, 4H), 1.70 (s, 11H), 1.59 (s, 2H). MS m/z (ESI): 407.3 [M+H].Compound TDI01261-1 (2.0 g, 8.58 mmol) and Compound TDI01249-2 (400 mg, 1.39 mmol),

Molecular Weight:233.27
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:233.116426730
Monoisotopic Mass:233.116426730
Topological Polar Surface Area:70.1
Heavy Atom Count:17
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes