Home Cart Sign in  
Chemical Structure| 1312929-42-2 Chemical Structure| 1312929-42-2

Structure of 1312929-42-2

Chemical Structure| 1312929-42-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1312929-42-2 ]

CAS No. :1312929-42-2
Formula : C5H7N3O2
M.W : 141.13
SMILES Code : O=C(C1=CC(N)=NN1)OC
MDL No. :MFCD09991917

Safety of [ 1312929-42-2 ]

Application In Synthesis of [ 1312929-42-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1312929-42-2 ]

[ 1312929-42-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 181585-93-3 ]
  • [ 1312929-42-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; for 24h; To a solution of methyl 3-nitro-lH-pyrazole-5-carboxylate (14A) (5 g, 29.22 mmol) in methanol (75 mL) was added Pd/C (10% on C, 0.6 g). The resulting mixture was hydrogenated at 50 psi for 24 h. After filtering the catalyst through a pad of Celite, the filtrate wasconcentrated in vacuum to dryness and the residue was purified by flash columnchromatography (silica gel, eluting with MeOH/CHCl3 0 to 20%) to furnish methyl 3 -amino- 1H- pyrazole-5-carboxylate (14B)(4.4 g, 100%) as an off-white solid; mp 134.1 C; 1H NMR (300 MHz, DMSO) delta 12.99-1 1.69 (bs, IH), 5.77 (s, IH), 5.03 (bs, 2H), 3.74 (s, 3H). MS (ES+) 142.2(M+l).
87% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 4h; To a stirred solution of methyl 3-nitro-lH-pyrazole-5-carboxylate(A59, 25.0 g, 146.19 mmol) in methanol(500 mL) was added Pd/C(3.80 g, 36.54 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 balloon pressure at room temperature for 4 h. After completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get methyl 3-amino-lH-pyrazole-5-carboxylate A60 as a pale yellow solid. Yield: 18.0 g(87%) LC-MS(ES) m/z : 142.16[M+H]+.
With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; 123B. Preparation of methyl 3-amino-1H-pyrazole-5-carboxylate A suspension of <strong>[181585-93-3]methyl 3-nitro-1H-pyrazole-5-carboxylate</strong> (10 g, 58.4 mmol) and 10% Pd on charcoal (1.2 g) in methanol (150 Ml) was stirred under 50 psi pressure of hydrogen gas for 16 h. The reaction mixture was filtered over a bed of Celite and the filtrate was concentrated to give 9.2 g of methyl 3-amino-1H-pyrazole-5-carboxylate which was used as such in the next reaction. MS (ESI) m/z 142.3 (M+H).
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 18h; To 14.0 g <strong>[181585-93-3]methyl 3-nitro-1H-pyrazole-5-carboxylate</strong> in 200 ml methanol are added 1.2 g Pd/C (10% w/w). The mixture is stirred under H2-atmosphere at room temperature for 18 h. The mixture is filtrated over kieselgur. The filtrate is concentrated and the crude product is used without further purification.MS (M+1): 141Characteristic 1H NMR (300 MHz, dDMSO) signals: 5.7 ppm (s, 1H); 3.8 ppm (s, 3H)
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 18h; Step3: Methyl 5,7-dihydroxy-6-phenylpyrazolo[1 ,5-a]pyrimidine-2-carboxylate; A solution of 5.Og Methyl 3-amino-1 H-pyrazole-5-carboxylate, 8.3ml_ diethyl- phenylmalonate and 5OmL diisopropylethylamine in 5OmL DMF was heated to 1500C for 40h. The solvent was removed, the solid residue was dissolved in 2- propanol the mixture was stirred for 3 hours. The desired product was filtered, dried and was used without further purification. MS (M+1): 286 Characteristic 1 H NMR (300MHz, d6-DMSO) signals: 6.0 (s, 1 H); 3.8 (s, 3H)
100 mg With palladium 10% on activated carbon; ammonium formate; In ethanol; at 70℃; for 1h; To a solution of methyl 3-nitro- 1H-pyrazole-5-carboxylate (500 mg) in Ethanol (0.25M) was added 10% Palladium on Carbon (0.1 eq) and ammonium fomiate (8 eq) and the reaction was heated for 1 hour at 70C then cooled to room temperature, filtered through celite, rinsed withMethanol and concentrated to dryness. The crude intermediate was suspended in DCM and extracted with water. To the organic layer was added 3 eq of MP-TsOH catch and release resin whereupon the mixture was stirred for 1 hour, filtered to collect resin then eluted with 7N Ammonia in MeOH and concentrated to dryness to afford 100 mg of methyl 3-amino-1H-pyrazole-5-carboxylate. To a solution of methyl3-amino-1H-pyrazole-5-carboxylate in dioxane was added di-tert-butyl dicarbonate (1.5 eq) and the reaction was heated at 120C overnight, then stirred at room temperature for 6 hours before the addition of imidazole (4.5 eq). The reaction mixture was subsequently refluxed at 130C for 2 hrs then stirred at room temperature overnight, concentrated to dryness, suspended in Ethyl acetate and extracted 3x with 0.25N HC1 solution, dried, filtered and concentrated to afford 427 mg ofmethyl 3-Qert-butoxycarbonylamino)-1H-pyrazole-5-carboxylate as a light pink solid. Similar to as described in General Procedure A, 3-(tert-butoxycarbonylamino)- 1H-pyrazole-5-carboxylate (200 mg) was reacted with 2-fluoro-4-iodo-pyridine to give methyl 5-(tert-butoxycarbonylamino)- 1 -(4-iodo-2-pyridyl)pyrazole-3-carboxylate. The crude material was used directly in subsequent reactions. To a solution of5-(tertbutoxycarbonylamino)-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate in DCM was added 4NHC1 in dioxane (10 eq). The reaction was stirred at room temperature for 30 minutes thenconcentrated to dryness to afford crude methyl5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate as the HC1 salt. Similar to as described inGeneral Procedure J, methyl 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate was reacted toafford 90 mg 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid which was used in the nextstep without purification. Similar as to described in General Procedure B, 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid was reacted with ammonium chloride to afford 90 mg of 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxamide which was used in the next reaction without purification.Similar to as described in General Procedure E, 5-amino-1-(4-iodo-2-pyridyl) pyrazole-3-carboxamide (90 mg) was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one to give 14mg of the title compound (15%). M-i-H = 341.0; 1H NMR (400 MHz, DMSO-d6) oe 8.44 (dd, J= 5.2, 0.8 Hz, 1H), 8.03- 8.00 (m,1H), 7.68 (s, 1H), 7.29, (dd, J= 5.1, 1.5 Hz, 1H), 7.21 (s, 1H), 6.89 (s, 2H), 6.63 (s, 1H), 5.72 (s,1H), 3.41 - 3.34 (m, 2H), 2.81 (s, 3H), 2.48 - 2.43 (m, 1H), 2.26 - 2.17 (m, 1H).

 

Historical Records

Technical Information

Categories