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Product Details of [ 1820-80-0 ]

CAS No. :1820-80-0 MDL No. :MFCD00005236
Formula : C3H5N3 Boiling Point : -
Linear Structure Formula :- InChI Key :JVVRJMXHNUAPHW-UHFFFAOYSA-N
M.W : 83.09 Pubchem ID :74561
Synonyms :

Calculated chemistry of [ 1820-80-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 22.99
TPSA : 54.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.2
Log Po/w (XLOGP3) : -0.13
Log Po/w (WLOGP) : 0.0
Log Po/w (MLOGP) : -0.72
Log Po/w (SILICOS-IT) : 0.56
Consensus Log Po/w : -0.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.89
Solubility : 10.7 mg/ml ; 0.129 mol/l
Class : Very soluble
Log S (Ali) : -0.56
Solubility : 22.6 mg/ml ; 0.272 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.76
Solubility : 14.3 mg/ml ; 0.173 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 1820-80-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3263
Hazard Statements:H302-H314-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1820-80-0 ]

* 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.

  • Upstream synthesis route of [ 1820-80-0 ]
  • Downstream synthetic route of [ 1820-80-0 ]

[ 1820-80-0 ] Synthesis Path-Upstream   1~26

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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018,
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1267 - 1273
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Reference: [1] Helvetica Chimica Acta, 1956, vol. 39, p. 986,988
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  • [ 826-85-7 ]
  • [ 1128-56-9 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 16, p. 2433 - 2436
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  • [ 1128-56-9 ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate; copper(ll) bromide In N,N-dimethyl-formamide at 190℃; for 0.333333 h; Microwave irradiation; Sealed tube 1 -phenyl- 1 H -pyrazol-3-amine 3-Amino-pyrazole (1 .0 g, 12.03 mmol), Cs2CO3 (3.92 g, 12.03 mmol), iodobenzene (3.68 g, 18.05 mmol), CuBr2 (0.268 g, 0.1 mmol), and DMF (4 ml_) were added to a 10-mL microwave vial. The vial was sealed and heated to 190 °C for 20 min (monitored by TLC). After cooling, the reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate (50 imL x 3). The organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with 0-40percent ethyl acetate and petroleum benzine, afforded the desired product, 1 -phenyl-1 -/-pyrazol-3-amine, as a brown solid (1 .53 g, 80percent).
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 6, p. 2067 - 2070
[2] Patent: WO2015/172196, 2015, A1, . Location in patent: Paragraph 00225
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Reference: [1] ChemCatChem, 2015, vol. 7, # 16, p. 2433 - 2436
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  • [ 4522-35-4 ]
Reference: [1] Patent: WO2007/35309, 2007, A1, . Location in patent: Page/Page column 62
[2] Patent: WO2017/117708, 2017, A1, . Location in patent: Page/Page column 95
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  • [ 6287-38-3 ]
  • [ 6334-18-5 ]
Reference: [1] Patent: US2003/22890, 2003, A1,
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  • [ 105-53-3 ]
  • [ 57489-70-0 ]
YieldReaction ConditionsOperation in experiment
77% With sodium ethanolate In ethanol at 80℃; for 16 h; Inert atmosphere Step A - Synthesis of pyrazolo[ l,5-a]pyrimidine-5,7-diol (lnt-9a)To lH-pyrazol-3-amine (12.3 g, 148.0 mmol) in EtOH (50 mL) was added diethyl malonate (25.0 mL, 164.7 mmol), 21 wtpercent NaOEt in EtOH (1 10 mL, 294.6 mmol) and additional EtOH (50 mL). The resulting reaction mixture was then heated at 800C under an atmosphere of argon for 16 hours, at which time the reaction was allowed to cool to room temperature. The reaction mixture was then concentrated in vacuo until almost dry, before H2O (500 mL) was added. Vigorous stirring aided the dissolution of solids, at which time cone. HCl was added until pH~2 was attained (precipitate formed). The precipitate was collected and dried by vacuum filtration giving pyrazolo[l,5-a]pyrimidine-5,7-diol (Int-9a) as a tan solid (17.13 g, 1 13.4 mmol, 77percent).
77% With sodium ethanolate In ethanol at 80℃; for 16 h; Inert atmosphere To lH-pyrazol-3-amine (12.3 g, 148.0 mmol) in EtOH (50 mL) was added diethyl malonate (25.0 mL5 164.7 mmol), 21wtpercent NaOEt in EtOH (1 10 mL, 294.6 mmol) and additional EtOH (50 mL). The resulting mixture was then heated at 80 C under an atmosphere of argon for 16 hours, at which time the reaction was allowed to cool to room temperature. The reaction mixture was then concentrated in vacuo until almost dry, before 3/40 (500 mL) was added. Vigorous stirring aided the dissolving of solids, at which time cone. HC1 was added until pH~2 was attained (solid precipitate formed). The precipitate was collected and dried by vacuum filtration giving pyrazolo[l,5-a]pyrimidine-5,7-diol as a tan solid (17.13 g, 113.4 mmol, 77percent).
Reference: [1] Patent: WO2011/2887, 2011, A1, . Location in patent: Page/Page column 86
[2] Patent: WO2012/27234, 2012, A1, . Location in patent: Page/Page column 39; 40
[3] Patent: US2011/294781, 2011, A1, . Location in patent: Page/Page column 20
[4] Patent: WO2012/27240, 2012, A1, . Location in patent: Page/Page column 47
[5] Patent: WO2012/47569, 2012, A1, . Location in patent: Page/Page column 41
[6] Patent: WO2012/47570, 2012, A1, . Location in patent: Page/Page column 41
[7] Patent: WO2013/16164, 2013, A1, . Location in patent: Page/Page column 54; 55
[8] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 126 - 132
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Reference: [1] Patent: EP2621926, 2017, B1,
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  • [ 34461-00-2 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With hydrogenchloride; zinc(II) chloride In ethanolReflux
Stage #2: for 1 h;
1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33percent) ( A) was isolated and purified by column chromatography.
27% at 90℃; for 16 h; To a solution of sodium nitromalonaldehyde monohydrate(1.23 g, 7.81 mmol) in water was added 1H-pyrazol-3-amine(0.84 g, 7.43 mmol). The mixture was stirred at 90 °C for 16 h andthen cooled to room temperature. The reaction solution wasadjusted to pH 5 and extracted by ethyl acetate (200 mL). Theorganic layer was dried over Na2SO4 and evaporated. The residuewas purified by silica gel chromatography (1percent MeOH in dichloromethane)to give 5-nitro-1H-pyrazolo [4,3-b]pyridine as a whitesolid (118 mg, 27percent). Rf: 0.23 (DCM/MeOH, 100/1, v/v). Mp:206-208 °C. 1H NMR (DMSO-d6, 400 MHz) d 14.40 (s, 1H), 9.35 (d,J 2.5 Hz, 1H), 9.21 (d, J 2.5 Hz, 1H), 8.46 (s, 1H). MS (ESI) m/z:162.8 [MH]-.
Reference: [1] Patent: US2013/29995, 2013, A1, . Location in patent: Paragraph 0372-0373
[2] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
  • 13
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  • [ 34461-00-2 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
33% With hydrogenchloride; zinc(II) chloride In ethanol for 1 h; Reflux 1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33 percent) (A) was isolated and purified by column chromatography.
Reference: [1] Patent: WO2013/13816, 2013, A1, . Location in patent: Page/Page column 73
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  • [ 63572-73-6 ]
Reference: [1] Patent: WO2018/171575, 2018, A1, . Location in patent: Page/Page column 24; 33; 35; 75
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  • [ 87-13-8 ]
  • [ 43024-61-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1347 - 1351
[2] Patent: US4081545, 1978, A,
  • 16
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  • [ 14339-33-4 ]
YieldReaction ConditionsOperation in experiment
42% With hydrogenchloride; copper dichloride In water; acetonitrile at 0℃; for 0.5 h; 3-Chloro-1H-pyrazole (1): Copper (II) chloride (65.0 g, 481 mmol) and cone. HCl (20 mL) were added to a solution of lH-pyrazol-3-amine (20.0 g, 241 mmol) in acetonitrile (600 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 30 min, then isopentyl nitrite (56.4 g, 481 mmol) was added dropwise. The mixture was stirred at room temperature for 2 days, and then quenched with aq. ammonia (10percent, 1 L). The aqueous phase was extracted with EtOAc (5 x 500 mL) and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane: EtOAc= 20: 1) to give the title compound (10.3 g, 42percent) as a green oil. 1H NMR (400 MHz, CDC13): δ 12.84 (bs, 1H), 7.62 (s, 1H), 6.29 (s, 1H).
Reference: [1] Patent: WO2018/85247, 2018, A1, . Location in patent: Paragraph 00296; 00297
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  • [ 927-63-9 ]
  • [ 274-71-5 ]
YieldReaction ConditionsOperation in experiment
65% for 6 h; Reflux Preparation of compound 23a: pyrazolo[1,5-a]pyrimidineA mixture of 1 H-pyrazol-3-ylamine (32 g, 0.386 mol) and (E)-3-dimethylamino- propenal (38.2 g, 0.386 mol) in EtOH (500 ml_) was refluxed for 6 h. The solvent was removed in vacuo and the residue was purified via column chromatography (petroleum ether/EtOAc = 10:1 -2:1 ) which gave the title compound 23a as a white solid (30 g, 65percent).
Reference: [1] Synthesis, 2006, # 1, p. 59 - 62
[2] Patent: WO2010/16005, 2010, A1, . Location in patent: Page/Page column 116
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  • [ 26621-44-3 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 7, p. 886 - 890
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  • [ 623-47-2 ]
  • [ 29274-22-4 ]
YieldReaction ConditionsOperation in experiment
36% at 110℃; Inert atmosphere A solution of 1H-pyrazol-3-ylamine (7 g, 84.24 mmol, 1 .00 equiv) and ethyl prop-2-ynoate (50 mL) in dioxane ( 1 0 g, 1 21 equiv) was stirred under nitrogen overnight at 110 "C. The reaction mixture was cooled to rt and the precipitated product was collected by filtration to give 4 g (36percent) of the title compound as a light brown solid 1H NMR (300 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.41 -8.44 (m, 1H), 7.71 (d. J = 18 Hz, 1H), 5.88 (d, J = 8. 1Hz, 1H), 5.77 (m, 1H)
36% at 110℃; Inert atmosphere A solution of 1H-pyrazol-3-ylamine (7 g, 84.24 mmol, 1 .00 equiv) and ethyl prop-2-ynoate (50 mL) in dioxane ( 1 0 g, 1 21 equiv) was sti rred under nitrogen overnight at 1 1 0 "C. The reaction mixture was cooled to rt and the precipitated product was collected by filtration to give 4 g (36percent) of the title compound as a light brown sol id1HNMR ( 300 MHz, DMSO-d6) δ 1 2.04 (s, 1H), 8.41 -8.44 (m, 1H), 7.71 (d. J = 18 Hz, 1H ), 5.88 (d, J = 8. 1Hz, 1H), 5.77 (m, 1H)
36% at 110℃; Inert atmosphere A solution of 1H-pyrazol-3-ylamine (7 g, 84.24 mmol, 1 .00 equiv) and ethyl prop-2-ynoate (50 mL) in dioxane ( 1 0 g, 1 21 equiv) was stirred under nitrogen overnight at 110 "C. The reaction mixture was cooled to rt and the precipitated product was collected by filtration to give 4 g (36percent) of the title compound as a light brown solid 1H NMR (300 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.41 -8.44 (m, 1H), 7.71 (d. J = 18 Hz, 1H), 5.88 (d, J = 8. 1Hz, 1H), 5.77 (m, 1H)
36% at 110℃; Inert atmosphere 0217] Step 1. 4H-Pyrazolor 5-alpyrimidin-5-one. A solution of lH-pyrazol-3-ylamine (7 g, 84.24 mmol, 1.00 equiv) and ethyl prop-2-ynoate (50 mL) in dioxane (10 g, 1.21 equiv) was stirred under nitrogen overnight at 110 °C. The reaction mixture was cooled to rt and the precipitated product was collected by filtration to give 4 g (36percent) of the title compound as a light brown solid. 1H NMR (300 MHz, DMSO-J6) δ 12.04 (s, 1H), 8.41-8.44 (m, 1H), 7.71 (d, J = 1.8 Hz, 1H), 5.88 (d, J = 8.1 Hz, 1H), 5.77 (m, 1H).

Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 41, p. 6168 - 6178
[2] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 142
[3] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 93
[4] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 68
[5] Patent: WO2013/130943, 2013, A1, . Location in patent: Paragraph 0217
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Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 41, p. 6168 - 6178
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  • [ 29274-22-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5521 - 5527
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  • [ 57489-77-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 15, p. 6700 - 6715
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YieldReaction ConditionsOperation in experiment
88%
Stage #1: With bromine In acetic acid at 0 - 5℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water
At 0-50C, a solution of 3-amino pyrazole (120mmol) in AcOH (22mL) was slowly added a solution of Br2 in AcOH (22mL) over a period of 2h. The reaction was complete immediately after the addition of Br2 solution (120mmol). To the reaction mixture was added CCl4 (8mL), stirred for 30min at rt. The precipitated solid was filtered and washed with additional CCl4 (8mL). The solid so obtained was dissolved in water (40 mL), adjusted to pH ~7.5 (using aq. NaHCO3 solution) and the precipitated solid was filtered and washed with water (8mL). The combined filtrates were also adjusted to pH ~8 (aq. Na2CO3 solution), extracted with EtOAc (80OmL), washed with brine solution <n="70"/>(20OmL), dried (Na2SO4), filtered and evaporated to obtain the desired compound as a yellow solid. The crude compound was stirred with CCl4 (2OmL), filtered and washed with acetone (5mL) and CCl4 (8mL), and dried under vacuum. The product was obtained as a pale yellow solid (17.2 g, 88 percent yield). TLC system: DCM/MeOH (9: 1). Rf value: 0.5. (M + H): 162.3.
Reference: [1] Patent: WO2009/85913, 2009, A1, . Location in patent: Page/Page column 68-69
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  • [ 2065-75-0 ]
  • [ 705263-10-1 ]
YieldReaction ConditionsOperation in experiment
58% at 20℃; for 3 h; At room temperature,3-amino-1H-pyrazole (120 mmol, 10 g)A solution in 50 ml of anhydrous acetic acid was added dropwise to bromomalonaldehyde (120 mmol, 18.9 g)In a suspension of 50 mL of anhydrous acetic acid,The resulting brown solution was stirred at room temperature for 3 hours.Evaporating acetic acid under reduced pressure,Adding chloroform to the residue;The organic phase is saturated with NaHCO3 solution,Washed with brine and dried over sodium sulfate.After the column, the product was obtained (14g, 58percent).
58% With acetic acid In ethanol at 80℃; for 1.5 h; Synthesis of 4-[6-(4-Piperazin-l-ylphenyl)pyrazolo[l ,5-a]pyrimidin-3-yllquinoline hydrochloride salt (13 HCH; A mixture of 2-bromomalondialdehyde (1.5 g, 10 mmol) and lH-pyrazol-3- ylamine (4b, 0.83 g, 10 mmol) in a mixture of EtOH (15 mL) and acetic acid (5 mL) was heated at 80 °C for 1.5 h. The reaction mixture was concentrated and the resulting residue purified by column chromatography using hexane/EtOAc (5:1 ) to give 15a (1.15 g, 58percent yield) as light yellow crystals.
42% at 20℃; for 3 h; Preparation 16-Bromo-pyrazolo[1 ,5-a]pyrimidine[00117] A solution of 3-amino-1 H-pyrazole (120 mmol, 10g) in 50ml of anhydrous acetic acid is added dropwise to a suspension of bromomalonaldehyde (120 mmol, 18.9 g) in 50 mL anhydrous acetic acid at room temperature. The resulting brown solution is stirred at room temperature for 3 hours, acetic acid is evaporated at reduced pressure and chloroform is added to the residue. The organic phase is washed with saturated solution of NaHCO3, brine, and dried over sodium sulfate. The product is purified by flash column chromatography (CH2CI2 : Et3N 100 : 0.5 as eluent, Rf=0.3) to yield the title compound (5 g, 42percent).
11% for 2 h; Heating / reflux Dissolve bromomalonaldehyde (Aldrich; 2.5 g, 16.5 mmol) and 3-aminopyrazole (Aldrich; 1.38 g, 16.5 mmol) in glacial acetic acid (25 ML) and reflux the resulting mixture under nitrogen for 2 h. Concentrate under reduced pressure. Dissolve the residue in absolute methanol (150 mL), vacuum filter through a pad diatomaceous earth and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from neat hexane to 50percent ethyl acetate/50percent hexane to obtain 365 mgs (11percent) of the subtitled compound as a light yellow solid. High Resolution Mass Spectrum: 197.9674 (M+1).

Reference: [1] Patent: CN108586464, 2018, A, . Location in patent: Paragraph 0031; 0038; 0039
[2] Patent: WO2009/114180, 2009, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2011/15343, 2011, A1, . Location in patent: Page/Page column 38-39
[4] Patent: WO2004/50659, 2004, A1, . Location in patent: Page 72
[5] Patent: WO2008/78100, 2008, A2, . Location in patent: Page/Page column 111-112
[6] Patent: WO2004/74290, 2004, A1, . Location in patent: Page 83
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3248 - 3252
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  • [ 20591-60-0 ]
  • [ 705263-10-1 ]
Reference: [1] Patent: WO2009/14620, 2009, A1, . Location in patent: Page/Page column 36; 24
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  • [ 2065-75-0 ]
  • [ 875781-17-2 ]
YieldReaction ConditionsOperation in experiment
11% for 2 h; Heating / reflux Preparation 6; 5 -Bromo- 1 H-pyrazolo [3 ,4-b] pyridine; Dissolve 2-bromomalonaldehyde (Aldrich; 2.5 g, 16.5 mmol) and3-aminopyrazole (Aldrich; 1.38 g, 16.5 mmol) in glacial acetic acid (25 mL) and reflux under nitrogen for 2 h. Concentrate under reduced pressure and dissolve the residue in absolute methanol (150 mL), vacuum filter through a pad of diatomaceous earth and concentrate under reduced pressure. Purify via chromatography (silica gel, hexane to 50percent ethyl acetate/50percent hexane) to obtain 365 mg (11percent) of the title compound as a light EPO <DP n="25"/>yellow solid. TOF MS ES+ exact mass calculated for C6H5N3Br (p+H): m/z =197.9667, Found: 197.9674.
Reference: [1] Patent: WO2006/52568, 2006, A2, . Location in patent: Page/Page column 23-24
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