4,7-DIAZA-1H-INDAZOLE
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4,7-DIAZA-1H-INDAZOLE
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CAS No:
272-60-6
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Formula:
C5H4N4
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Chemical Name:
4,7-DIAZA-1H-INDAZOLE
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Synonyms:
4,7-DIAZA-1H-INDAZOLE;1H-pyrazolo[3,4-b]pyrazine;2H-Pyrazolo[3,4-b]pyrazine;7H-Pyrazolo[3,4-b]pyrazine;24977-38-6;399-62-2;pyrazolopyrazine;SCHEMBL219870;SCHEMBL19269974;CTK8B5945
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CAS No:
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4,7-DIAZA-1H-INDAZOLE Use and Manufacturing
[A] (rac) -tert-Butyl ( (1R 3S) -3- ( (5-fluoro-2- (1H-pyrazolo [3 4-b] pyrazin-1-yl) pyrimidin-4-yl) amino) cyclohexyl) carbamate[0752][0753]To a solution of (rac) -tert-butyl N- [ (1R 3S) -3- [ (2-chloro-5-fluoro-pyrimidin-4-yl) amino] cyclohexyl] carbamate (Example 1/Step A 610 mg 2 mmol) in dioxane (10 mL) was added 1H-pyrazolo [3 4-b] pyrazine (Intermediate A-7 600 mg 5 mmol) (1R 2R) -cyclohexane-1 2-diamine (350 mg 3 mmol) Cul (600 mg 3.0 mmol) and K3PO4(1.05 g 5 mmol) . The resuting reaction mixture was stirred at 120 for 12 h. After cooling to room temperature the reaction mixture was filtered and the filtrate was concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (DCM/MeOH 501) to afford the title compound (420 mg 39yield) as a brown solid. MS 429.0 [M+H]+.To a solution of the crude reactant SA (249.5 mg, 0.629 mmol, theoretical amount) in anhydrous THF (5 mL) was added lH-pyrazolo[3, 4-b]pyrazine (151 mg, 1.256 mmol) followed by potassium carbonate (174 mg, 1.256 mmol) and the resulting solution was stirred at 25 C overnight. Then the solution was diluted with ethyl acetate (200 mL) and the resulting solution was washed with brine (2x 100 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford product SA-28 (17.3 mg, 0.0396 mmol, Yield=6.3% (2 steps)) and product SA-29 (67.5 mg, 0.155 mmol, Yield=25% (2 steps)) as white solid. Compound SA-28: 1H NMR (400 MHz, CDCI3) 5(ppm): 8.64 (IH, d), 8.56 (IH, d), 8.27 (IH, s), 5.35 (IH, AB), 5.23 (IH, AB), 2.70 (IH, t0.72 (3H, s). LCMS: rt = 2.22 mm, m/z = 437.2 [M+H]+Compound SA-29 : 1H NMR (400 MHz, CDCI3) 5(ppm): 8.59 (IH, d), 8.44 (IH, d), 8.34 (IH, s), 5.34 (IH, AB), 5.28 (IH, AB), 2.71 (IH, t), 0.73 (3H, s). LCMS: rt = 2.37 mm, m/z = 437.2 [M+H]+
Computed Properties
Molecular Weight:120.11
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:120.043596145
Monoisotopic Mass:120.043596145
Topological Polar Surface Area:54.5
Heavy Atom Count:9
Complexity:105
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
