Tert-Butyl 2-(((Benzyloxy)Carbonyl)Amino)-6,7-Dihydropyrazolo[1,5-A]Pyrazine-5(4H)-Carboxylate synthesis

6synthesis methods

Product Name:Tert-Butyl 2-(((Benzyloxy)Carbonyl)Amino)-6,7-Dihydropyrazolo[1,5-A]Pyrazine-5(4H)-Carboxylate
CAS Number:1209488-61-8
Molecular formula:C19H24N4O4
Molecular Weight:372.42

1209492-73-8 Synthesis

5-N-Boc-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid

1209492-73-8
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100-51-6 Synthesis

100-51-6
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Tert-Butyl 2-(((Benzyloxy)Carbonyl)Amino)-6,7-Dihydropyrazolo[1,5-A]Pyrazine-5(4H)-Carboxylate

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Yield:1209488-61-8 63%

Reaction Conditions:

with diphenyl phosphoryl azide;triethylamine in toluene at 100; for 4 h;Inert atmosphere;

Steps:

2-1.7

Step 7 To a suspension of Compound 18 (1.93 g, 7.22 mmol) in toluene (30 mL), under nitrogen atmosphere, benzylalcohol (0.90 mL, 8.67 mmol), diphenylphosphoryl azide (1.87 mL, 8.67 mmol), and triethylamine (1.30 mL, 9. 39 mmol) were added. The solution was then stirred at 100°C for 4 hours. Water was added to the reaction solution and then extracted with ethyl acetate. The extract was washed sequentially with water and saturated brine. The solution was dried with anhydrous magnesium sulfate and then concentrated in vacuo. The residue was washed with methanol to yield Compound I-158 (1.70 g, 63%). LC/MS (Method D): 1.89 min, [M+H]⁺ = 373 ¹H-NMR (DMSO-d₆) δ: 9.98 (1H, s), 7.39-7.32 (5H, m), 6.17 (1H, s), 5.12 (2H, s), 4.54 (2H, s), 3.93 (2H, t, J = 5.0 Hz), 3.78 (2H, t, J = 5.0 Hz), 1.43 (9H, s).

References:

EP2327704,2011,A1 Location in patent:Page/Page column 53

1H-Pyrazole-3,5-dicarboxylic acid, 1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-, 3,5-dimethyl ester

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1H-Pyrazole-3,5-dicarboxylic acid, 1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-, 3-methyl ester

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1H-Pyrazole-3-carboxylic acid, 1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-5-(hydroxymethyl)-, methyl ester

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1H-Pyrazole-3-carboxylic acid, 5-(chloromethyl)-1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-, methyl ester

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References