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Chemistry
Heterocyclic Building Blocks
Pyrazoles
Furans ∩ Aromatic Heterocycles
5-(Furan-2-yl)-1H-pyrazol-3-amine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
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Furans Amines Aromatic Heterocycles
Furans ∩ Aromatic Heterocycles
Pyrazoles ∩ Aromatic Heterocycles pyrazol-amine Aromatic Heterocycles ∩ Amines Pyrazoles ∩ Furans Furans ∩ Amines Pyrazoles ∩ Amines

[ CAS No. 96799-02-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 96799-02-9
Chemical Structure| 96799-02-9
Chemical Structure| 96799-02-9
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Quality Control of [ 96799-02-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 96799-02-9 ]

Product Details of [ 96799-02-9 ]

CAS No. :96799-02-9 MDL No. :MFCD00082696
Formula : C7H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :XJNZHICOWTVWOX-UHFFFAOYSA-N
M.W : 149.15 Pubchem ID :523183
Synonyms :

Calculated chemistry of [ 96799-02-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.69
TPSA : 67.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : 0.63
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : -0.2
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 0.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.77
Solubility : 2.54 mg/ml ; 0.017 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 3.5 mg/ml ; 0.0235 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.386 mg/ml ; 0.00259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 96799-02-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 96799-02-9 ]

* 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 [ 96799-02-9 ]

[ 96799-02-9 ] Synthesis Path-Downstream   1~47

  • 1
  • [ 3542-00-5 ]
  • [ 96799-02-9 ]
  • [ 96799-07-4 ]
Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 7 - 10
  • 2
  • [ 96799-02-9 ]
  • [ 96799-00-7 ]
  • [ 96799-16-5 ]
Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 7 - 10
  • 3
  • [ 96799-02-9 ]
  • [ 96799-01-8 ]
  • [ 96799-14-3 ]
Reference： [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 7 - 10
  • 4
  • [ 442549-32-8 ]
  • [ 96799-02-9 ]
  • [ 442548-32-5 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 6 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (5-furan-2-yl-1H-pyrazol-3-yl)-amide. This compound was prepared from 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) and commercially available <strong>[96799-02-9]5-furan-2-yl-1H-pyrazol-3-ylamine</strong> (Maybridge) as prepared in example 1, yielding a yellow solid. MS (M+H) m/z=420.
Example 6 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (5-furan-2-yl-1H-pyrazol-3-yl)-amide. This compound was prepared from 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) and commercially available <strong>[96799-02-9]5-furan-2-yl-1H-pyrazol-3-ylamine</strong> (Maybridge) as prepared in example 1, yielding a yellow solid. MS (M+H) m/z=420.
Example 6 8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (5-furan-2-yl-1H-pyrazol-3-yl)-amide This compound was prepared from 8-(4Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) and commercially available <strong>[96799-02-9]5-furan-2-yl-1H-pyrazol-3-ylamine</strong> (Maybridge) as prepared in example 1, yielding a yellow solid. MS (M+H) m/z=420.
Reference： [1]Patent: US2003/13708,2003,A1
[2]Patent: US2004/87575,2004,A1
[3]Patent: US2004/110745,2004,A1
  • 5
  • [ 96799-02-9 ]
  • [ 265107-68-4 ]
  • 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 4 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting 3-amino-5-(2-furyl)-pyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one (0.10 gms.) is reacted with 0.1480 gms. of 3-amino-5-(2-furyl)-pyrazole by refluxing in tetrahydrofuran (2.5 mL).
Reference： [1]Patent: US6559173,2003,B1
  • 6
  • Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one [ No CAS ]
  • [ 96799-02-9 ]
  • 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-4-methyl-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 7 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-4-methyl-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and substituting 3-amino-5-(2-furyl)-pyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one (0.110 gms.) is reacted with 0.2065 gms. of 3-amino-5-(2-furyl)-pyrazole by refluxing in tetrahydrofuran (2.5 mL).
Reference： [1]Patent: US6559173,2003,B1
  • 7
  • Z-3-[(hydroxy)-methylene]-5-fluoro-1,3-dihydro-indol-2-one [ No CAS ]
  • [ 96799-02-9 ]
  • 5-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 27 5-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-5-fluoro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 3-amino-5-(2-furyl)-pyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-5-fluoro-1,3-dihydro-indol-2-one (0.050 gms.) is reacted with 0.085 gms. of 3-amino-5-(2-furyl)-pyrazole by refluxing in tetrahydrofuran (1.5 mL).
Reference： [1]Patent: US6559173,2003,B1
  • 8
  • Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one [ No CAS ]
  • [ 96799-02-9 ]
  • 6-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 50 6-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and <strong>[96799-02-9]5-furan-2-yl-1H-pyrazol-3-ylamine</strong> for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one (0.033 gms.) is reacted with 0.061 gms. <strong>[96799-02-9]5-furan-2-yl-1H-pyrazol-3-ylamine</strong> by refluxing in tetrahydrofuran (0.88 mL) to afford the named compound in the amount of 0.0263 gms.
Reference： [1]Patent: US6559173,2003,B1
  • 9
  • Z-3-[(hydroxy)-methylene]-5-chloro-1,3-dihydro-indol-2-one [ No CAS ]
  • [ 96799-02-9 ]
  • 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-5-chloro-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 10 3-[(5-Furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-5-chloro-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-5-chloro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and substituting 3-amino-5-(2-furyl)-pyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-5-chloro-1,3-dihydro-indol-2-one is reacted with 0.280 gms. 3-amino-5-(2-furyl)-pyrazole by refluxing in tetrahydrofuran.
Reference： [1]Patent: US6559173,2003,B1
  • 10
  • [ 7252-83-7 ]
  • [ 96799-02-9 ]
  • [ 130598-93-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ammonium hydroxide; sodium chloride; In 1,4-dioxane; N-methyl-acetamide; ethanol; mineral oil; EXAMPLE 22 6-(2-Furyl)-1H-imidazo[1,2-b]pyrazole A solution of 2.0 g of 5-(2-furyl)-3-aminopyrazole in 5 ml of dimethylformamide was slowly added dropwise at room temperature, whilst stirring, to 0.59 g of a 55% w/w suspension of sodium hydride in mineral oil, which itself was suspended in 15 ml of dimethylformamide, and the resulting mixture was stirred for 1 hour at room temperature. 2.7 g of 2,2-dimethoxyethyl bromide were then added, and the mixture was allowed to react at 60 to 70 C. for 4 hours. At the end of this time, the resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 1.2 g of an intermediate compound as an oil. A mixture of 1.2 g of this intermediate compound, 10 ml of a 4N solution of hydrogen chloride in dioxane and 4 ml of ethanol was heated under reflux for 20 minutes, after which the reaction mixture was poured into ice water and made basic by the addition of aqueous ammonia. The mixture was then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, and the product was recrystallized from a mixture of ethyl acetate and hexane, to afford 0.44 g of the title compound as pale brown needle-like crystals, melting at 186 to 188 C. Elemental analysis: Calculated for C9 H7 N3 O: C, 62.42%; C, 4.07%; N, 24.27%. Found: C, 62.36%; H, 4.23%; N, 24.14%.
Reference： [1]Patent: US5232939,1993,A
  • 11
  • [ 96799-02-9 ]
  • [ 330601-48-4 ]
  • 2-(5-amino-3-furan-2-yl-pyrazol-1-yl)-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; Synthesis of 2-(5-Amino-3-furan-2-yl-pyrazol-1-yl)-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone Protocol T was followed using <strong>[96799-02-9]3-Furan-2-yl-2H-pyrazol-5-ylamine</strong>, K2CO3, 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using 100% ethyl acetate afforded the title compound as a white solid. 1H NMR (400 MHz, CD6CO) delta 7.48-7.52 (m, 1H), 6.98-7.06 (m, 2H), 6.52-6.56 (m, 2H), 6.44-6.48 (m, 2H), 5.74 (s, 1H), 4.98 (s, 2H), 3.68-3.88 (m, 4H), 3.12-3.24 (m, 4H). MS (ES) M+H) expected=369.4, found 370.1.
Reference： [1]Patent: US2004/162282,2004,A1
  • 12
  • [ 638-07-3 ]
  • [ 96799-02-9 ]
  • [ 1028843-23-3 ]
YieldReaction ConditionsOperation in experiment
In acetic acid; at 80℃; for 3h; Intermediate G: 5-Chloromethyl-2-furan-2-yl-pyrazolo[1 ,5-a]pyrimidin-7-olA suspension of 500 mg of 3-amino-5-(2-furyl)pyrazole and 0.47 ml of 4-chloro-3-oxo-butyric acid ethyl ester in 2.5 ml of glacial AcOH is heated at 80 C for 3 hours. The reaction mixture obtained is cooled to RT, the mixture is diluted with EtOAc and a precipitate is collected by filtration, washed with EtOAc and dried. The title compound is obtained
Reference： [1]Patent: WO2008/62026,2008,A1 .Location in patent: Page/Page column 32
  • 13
  • [ 4971-56-6 ]
  • [ 66-77-3 ]
  • [ 96799-02-9 ]
  • [ 1099638-28-4 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In ethanol at 82℃; for 15h; Heating / reflux; 5.5.D; 17 To a solution of 1H-2-amino-4-(2-yl-furan)pyrazole (746 mg, 5.0 mmole) in ethanol (15 ml) at 82° C. was added triethylamine (0.2 ml, 1.4 mmole) followed by 1-naphthaldehyde (0.682 ml, 5.0 mmole) and then tetronic acid (0.50 g, 5.0 mmole). The clear solution mixture was maintained at reflux for 15 h. A precipitate had formed and the mixture was cooled to room temperature. The mixture was filtered and washed with ethanol and ethyl ether to provide the desired product (1.38 g, 75%) as a white powder. 1H NMR (400 MHz; DMSO-d6) δ 12.7 (bs, 1H); 10.47 (bs, 1H); 7.80 (d, 1H, J=9.3 Hz); 7.72 (d, 1H, J=8.6 Hz); 7.60-7.40 (bs, m, 2H); 7.40-7.20 (m, 5H); 7.38 (at, 1H, J=7.4 Hz); 6.30 (bs, 1H); 6.1 (bs, 1H); 5.9 (bs, 1H); 4.87 (s, 2H). LC MS shows MH+ at 370 and 2 MH+ at 739.
Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - US2009/12103, 2009, A1 Location in patent: Page/Page column 39
  • 14
  • [ 96799-02-9 ]
  • [ 874-42-0 ]
  • [ 105-45-3 ]
  • [ 1245236-05-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4395 - 4398
  • 15
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 140-75-0 ]
  • [ 1258211-97-0 ]
YieldReaction ConditionsOperation in experiment
9% Example 9 To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added 3- amino-5-(2-furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 1- methylpiperazine (0.12 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and allowed to stir at room temperature for 3 hours. 4- fluorobenzylamine (0.37 mL, 3.26 mmol) and DIPEA (0.57 mL, 2.26 mmol) were added to the mixture and the mixture was stirred at room temperature overnight. Saturated NaHCtheta3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated.The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 9 as light yellow solid (66 mg, 9 %). 1H NMR (400 MHz, DMSO-d6) delta 12.61 (bs, 1H, NH), 9.90 (bs, 1Eta, NH), 9.14-9.01 (d, 1Eta, NH), 7.83-5.96 (m, 8Eta, Ar-H), 4.45 (bs, 2Eta, CH2), 3.67 (bs, 4Eta, 2CH2), 2.28 (bs, 4Eta, 2CH2), 2.17 (s, 3Eta, CH3); ESI-MS: calcd for (C22Eta24FN9O) 449, found 450 [M+H]+. HPLC: retention time: 16.58 min. purity: 100%
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 64
  • 16
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 100-46-9 ]
  • [ 1258212-00-8 ]
YieldReaction ConditionsOperation in experiment
13% Example 12To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added benzylamine (0.18 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.36 mL, 3.26 mmol) and DIPEA (0.57 mL, 3.26 mmol) were added to the mixture and the mixture was heated with microwave initiator at60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 12 as white solid (90 mg, 13 %). 1H NMR (400 MHz, DMSO-d6) delta 12.62 (s, 1H, NH), 9.92 (bs, 1Eta, NH), 9.14 (bs, 1Eta, NH),7.84-6.53 (m, 8Eta, Ar-H), 5.98 (bs, 1Eta, Ar-H), 4.49 (s, 2Eta, CH2), 3.70 (s, 4Eta, 2CH2), 2.30 (s, 4Eta, 2CH2), 2.19 (s, 3Eta, CH3); ESI-MS: calcd for (C22Eta24N9O) 431, found 432 [M+H]+. HPLC: retention time: 29.47 min. purity: 99%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 66
  • 17
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 100-53-8 ]
  • [ 1258212-02-0 ]
YieldReaction ConditionsOperation in experiment
34% Example 15To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added benzylmercaptan (0.19 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.36 mL, 3.26 mmol) and DIPEA (0.57 mL, 3.26 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 15 as white solid (250 mg, 34 %). 1H NMR (400 MHz, DMSOd6) delta 12.83 (s, 1H, NH), 9.92 (bs, 1Eta, NH), 7.74-6.59 (m, 9Eta, Ar-H), 4.34 (s, 2Eta, CH2), 3.75 (s, 4Eta, 2CH2), 2.34 (s, 4Eta, 2CH2), 2.29 (s, 3Eta, CH3); ESI-MS: calcd for (C22Eta24N8OS) 448, found 449 [M+H]+. HPLC: retention time: 20.34 min. purity: 99%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 68
  • 18
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 15894-04-9 ]
  • [ 96799-02-9 ]
  • [ 1258211-99-2 ]
YieldReaction ConditionsOperation in experiment
70% Example 11To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added 3- amino-5-(2-furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 1- methylpiperazine (0.12 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and allowed to stir at room temperature for 3 hours. 4-fluorobenzyl mercaptan (0.40 mL, 3.26 mmol) and DIPEA (0.57 mL, 2.26 mmol) were added to the mixture and the mixture was stirred at room temperature overnight. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 11 as light yellow solid (530 mg, 70 %). 1H NMR (400 MHz, DMSO-d6) delta 12.84 (s, 1H, NH), 9.94 (bs, 1Eta, NH), 7.75 (bs, 1Eta, Ar-H), 7.47 (bs, 2Eta, Ar-H), 7.12 (t, J= 8.8 Hz, 2H, Ar-H), 6.77-6.59 (m, 3Eta, Ar-H), 4.34 (s, 2Eta, CH2), 3.74 (bs, 4Eta, 2CH2), 2.34 (bs, 4Eta, 2CH2), 2.20 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 466, found 467 [M+H]+. HPLC: retention time: 21.31 min. purity: 97%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 65-66
  • 19
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 68285-27-8 ]
  • [ 1258212-03-1 ]
YieldReaction ConditionsOperation in experiment
11% Example 18To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) was added 4- fluorophenyl-2-ethylamine (0.16 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 18 as white solid (65 mg, 11 %). 1HNMR (400 MHz, DMSO-d6,80C) delta 12.48 (bs, 1H, NH), 9.52 (bs, 1Eta, NH), 8.55 (bs, 1Eta, NH), 7.71-5.96 (m, 8Eta, Ar-H), 5.12 (bs, 1Eta, CH), 3.67 (b, 4Eta, 2CH2), 2.30 (bs, 4Eta, 2CH2), 2.21 (s, 3Eta, CH3), 1.47 (s, 3Eta, CH3), 1.45 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 463, found 464 [M+H]+. HPLC: retention time: 16.82 min. purity: 95%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 69-70
  • 20
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 1258212-09-7 ]
YieldReaction ConditionsOperation in experiment
14% Example 13 To a solution of cyanuric chloride (200 mg, 1.09 mmol) in THF (16.0 mL) was added dropwise a solution of 3-amino-5-(2-furyl)pyrazole (162 mg, 1.09 mmol) and DIPEA (0.19 mL, 1.09 mmol) in THF (5 mL) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 1-metyl piperazine (0.12 mL, 1.09 mmol) and DIPEA (0.19 mL, 1.30 mmol) were added to the mixture. The mixture was allowed to stir at room temperature for 3h. The solids were filtered off to give compound 13 as white solid (110 mg, 14 %). %). 1H NMR (400 MHz, DMSO-d6) delta 12.92 (s, 1H, NH), 10.38 (s, 1Eta, NH), 7.76 (s, 1Eta, Ar-H), 6.81-6.61 (m, 3Eta, Ar-H), 3.77-3.72 (m, 4Eta, 2CH2), 2.38-2.35 (m, 4Eta, 2CH2), 2.21 (2, 3Eta, CH3); ESI-MS: calcd for (C15Eta17C1N8O) 360, found 361 [M+H]+.
14% A solution of 3-amino-5-(2-furyl)pyrazole (162 mg, 1.09 mmol) and DIPEA (0.19 mL, 1.09 mmol) in THF (5 mL) was added dropwise to a solution of cyanuric chloride (200 mg, 1.09 mmol) in THF (16.0 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. Then, 1-metyl piperazine (0.12 mL, 1.09 mmol) and DlPEA (0.19 mL, 1.30 mmol) were added to the mixture. The mixture was allowed to stir at room temperature for 3 hours. The solids were filtered off to give compound 11 as white solid (1 10 mg, 14 %). %). 1H NMR (400 MHz, DMSOd6) delta 12.92 (s, IH, NH), 10.38 (s, IH, NH), 7.76 (s, IH, Ar-H), 6.816.61 (m, 3H, Ar-H), 3.77-3.72 (m, 4H, 2CH2), 2.38-2.35 (m, 4H, 2CH2), 2.21 (2, 3H, CH3); ESI-MS: calculated for (C15Hi7ClN8O) 360, found 361 [M+H]+.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 66-67
[2]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 67
  • 21
  • [ 109-01-3 ]
  • [ 761390-58-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 1258212-07-5 ]
YieldReaction ConditionsOperation in experiment
15% Example 22To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 niL) was added (R)- l-(4-fluorophenyl)-2-ethylamine (0.16 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3- amino-5-(2-furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCtheta3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 22 as white solid as light brown solid (88 mg, 15 %). 1H NMR (400 MHz, DMSO-d6,80C) delta 12.48 (bs, 1H, NH), 9.53 (bs, 1Eta, NH), 8.58 (bs, 1Eta, NH), 7.65-6.04 (m, 8Eta, Ar-H), 5.12 (bs, 1Eta, CH), 3.68 (bs, 4Eta, 2CH2), 2.34 (bs, 4Eta, 2CH2), 2.23 (s, 3Eta, CH3), 1.47 (s, 3Eta, CH3), 1.45 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 463, found 464 [M+H]+. HPLC: retention time:
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 72-73
  • 22
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 405-66-3 ]
  • [ 96799-02-9 ]
  • [ 1258211-98-1 ]
YieldReaction ConditionsOperation in experiment
12% Example 10To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added 3- ammo-5-(2-furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 1- methylpiperazine (0.12 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and allowed to stir at room temperature for 3 hours. 4-fluoro-N- methyl-benzylamine (0.43 mL, 3.26 mmol) and DIPEA (0.57 mL, 2.26 mmol) were added to the mixture and the mixture was stirred at room temperature overnight.Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 10 as light yellow solid (90 mg, 12 %). 1H NMR (400 MHz, DMSO-dg) delta 12.63 (bs, 1H, NH), 9.28 (bs, 1Eta, NH), 7.70 (s, 1Eta, Ar-H), 7.35-7.09 (m,5Eta, Ar-H), 6.72-6.58 (m, 2Eta, Ar-H), 4.78 (s, 2Eta, CH2), 3.71 (bs, 4Eta, 2CH2), 3.04 (s, 3Eta, CH3), 2.32 (bs, 4Eta, 2CH2), 2.20 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 463, found 464 [M+H]+. HPLC: retention time: 19.98 min. purity: 97%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 64-63
  • 23
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • (S)-3-fluoro-α-methylbenzylamine [ No CAS ]
  • [ 1258212-06-4 ]
YieldReaction ConditionsOperation in experiment
9% Example 21 To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) was added (S)- l-(4-fluorophenyl)ethylamine (0.16 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino- 5-(2-furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1-methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 21 as light brown solid (52 mg, 9 %). 1H NMR (400 MHz, DMSO-d6,80C) delta 12.46 (bs, 1H, NH), 9.52 (bs, 1Eta, NH), 8.55 (bs, 1Eta, NH), 7.63-6.04 (m, 8Eta, Ar-H), 5.12 (bs, 1Eta, CH), 3.67 (bs, 4Eta, 2CH2), 2.30 (bs, 4Eta, 2CH2), 2.21 (s, 3Eta, CH3), 1.47 (s, 3Eta, CH3), 1.45 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 463, found 464 [M+H]+. HPLC: retention time: 17.10 min. purity: 99%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 72
  • 24
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 585-32-0 ]
  • C24H28FN9O [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% Example 23To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) was added cumylamine (0.18 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 23 as light brown solid (140 mg, 24%). 1H NMR (400 MHz, DMSO-d6) delta 12.88 (bs, 1H, NH), 9.87 (bs, 1Eta, NH), 7.88 (bs, 1Eta,NH), 7.67-5,91 (m, 9Eta, Ar-H), 3.52-3.20 (m, 4Eta, 2CH2), 2.32-1.96 (m, 7Eta, 2CH2, CH3), 1.67 (s, 3Eta, CH3), 1.49 (s, 3Eta, CH3); ESI-MS: calcd for (C24Eta29N9O) 459, found 460 [M+H]+. HPLC: retention time: 19.16 min. purity: 99%.
Reference： [1]Patent: WO2010/144394,2010,A1 .Location in patent: Page/Page column 73-74
  • 25
  • [ 109-01-3 ]
  • [ 533-30-2 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 1258222-99-9 ]
YieldReaction ConditionsOperation in experiment
34% 6- amino-benzothiazole (188 mg, 1.25 mmol) and DIPEA (0. 22 mL, 1.25 mmol) were added to a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) at 0 0C. The reaction mixture was stirred at 0 0C to room temperature for 2 hours. 3-amino-5-(2- furyl) pyrazole (187 mg, 1.25 mmol) and DIPEA (0.22 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 0C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column and eluted with 0- 5 % MeOH/DCM which afforded compound 37 as a white solid (200 mg, 34%). 1H NMR (400 MHz, DMSO-d6) delta 12.86 (bs, IH, NH), 10.99 (bs, IH, NH), 9.61 (bs, IH, NH), 9.21 - 6.59 (m, 8H, Ar-H), 4.68 (bs, 2H, CH2), 3.43 (bs, 2H, CH2), 3.09 (bs, 4H, 2CH2), 2.76 (s, 3H, CH3); ESI-MS: calculated for (C22H22Ni0OS) 474, found 475 [M+H]+. HPLC: retention time: 14.52 min. purity: 97%.
Reference： [1]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 82
  • 26
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 96799-02-9 ]
  • [ 108-98-5 ]
  • [ 1258222-74-0 ]
YieldReaction ConditionsOperation in experiment
14% To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added thiophenol (0.17 mL, 1.63 mmol) and DIPEA (0.28 mL, 1.63 mmol) at 0 C. The reaction mixture was stirred at 0 0C to room temperature for 2 hours. After starting material was consumed, 3-amino-3(2-furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.28 mL, 1.63 mmol) was added at O C. The mixture was stirred at room temperature for 3 additional hours. 1-methylpiperazine (0.27 mL, 2.45 mmol) and DlPEA (0.43 mL, 2.45 mmol) were added to the above mixture and allowed to stir at room temperature for overnight. Saturated NaHCC>;3 in water was added and the mixture was extracted by ethyl acetate. The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM to afford compound 9 as light yellow solid (100 mg, 14 %). IH NMR (400 MHz, DMSO-d6) delta 12.69 (bs, IH, NH), 9.79 (s, IH, NH), 7.79 (bs, I H, NH), 7.61 (bs, 2H, Ar-H), 7.45 (s, 3H, Ar-H), 6.60 (s-lH, Ar-H), 5.98 (bs,lH, Ar-H), 3.70 (bs, 4H, 2CH2), 2.31 (bs, 4H, 2CH2), 2.18 (s, 3H,CH3); ESl -MS: calculated for (C2,H22N80S) 434, found 435 [M+H]+. HPLC: retention time: 18.68 min. purity: 99%.
Reference： [1]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 65-66
  • 27
  • [ 109-01-3 ]
  • [ 108-77-0 ]
  • [ 54060-30-9 ]
  • [ 96799-02-9 ]
  • [ 1258222-98-8 ]
YieldReaction ConditionsOperation in experiment
24% 3- Ethynylaniline (146 mg, 1.25 mmol) and DIPEA (0. 22 mL, 1.25 mmol) were added to a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. 3-amino-5-(2-furyl) pyrazole (187 mg, 1.25 mmol) and DIPEA (0.22 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 0C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column and eluted with 0- 5 % MeOH/DCM which afforded compound 36 as light brown solid (130 mg, 24%). 1H NMR (400 MHz, DMSO-d6) delta 12.75 (bs, IH, NH), 10.19-9.44 (m, 2H, NH), 7.83- 6.06 (m, 8H, Ar- H), 4.14-4.04 (m, IH, CH), 3.77 (s, 4H, 2CH2), 2.37 (s, 4H, 2CH2), 2.22 (s, 3H, CH3); ESI- MS: calculated for (C23H23N9O) 441 , found 442 [M+H]+. HPLC: retention time: 15.31 min. purity: 95%.
Reference： [1]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 81-82
  • 28
  • [ 109-01-3 ]
  • [ 1258223-00-5 ]
  • [ 96799-02-9 ]
  • [ 1258222-71-7 ]
YieldReaction ConditionsOperation in experiment
26% To a solution of compound 2 (300 mg, 0.88 mmol) in THF (5 mL) a solution of 3- amino-5-92-furyl)pyrazole (105 mg, 0.70 mmol) and DIPEA (0.16 mL, 0.88 mmol) was added in 10-20 mL microwave vial. Vial was sealed with a cap and the mixture was allowed to stir at 150 0C for 5 minutes in the microwave synthesizer. Next, 1 -methyl piperazine (0.15 mL, 1.32 mmol) and DIPEA (0.23 mL, 1.32 mmol) were added to the above mixture and allowed to stir at 60 0C for 10 min. in the microwave synthesizer. The solvents were evaporated and the residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM obtaining compound 5 as off white solid (120 mg, 26 %). 1H NMR (400 MHz, DMSOd6) 5 12.66 (bs, IH, NH), 10.37 (s, IH, NH), 9.79 (s, IH, NH), 7.71 (bs, 3H; Ar-H), 7.51 (d, J = 8.4 Hz, IH, Ar-H), 6.07-6.01 (bs, IH, Ar-H), 3.70 (bs, 4H, 2CH2), 2.33 (m, 4H, 2CH2), 2.20 (s, 3H, CH3), 1.85-1.78 (m, IH, CH), 1.84-1.82 (m, 4H, Ar-H); ESI-MS: calculated for (C25H27N9OS2) 517, found 518 [M+H]+. HPLC: retention time: 17.10 min. purity: 100%.
Reference： [1]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 63
  • 29
  • [ 109-01-3 ]
  • [ 1258223-02-7 ]
  • [ 96799-02-9 ]
  • [ 1258222-92-2 ]
YieldReaction ConditionsOperation in experiment
32% DIPEA (0.13 mL, 0.65 mmol) and 5-(furan-2-yl)-lH-pyrazol-3-amine (87.4 mg, 0.586 mmol) were added to a suspension of compound 4 (0.2g, 0.588 mmol) in THF (12 mL). The mixture was heated at 150 C for 10 minutes using microwave initiator. A solution of N-Methylpiperazine (70.4 mg, 0.703 mmol) and DIPEA ((0.13 mL, 0.65 mmol) in THF (5 mL) was added to the above vial at room temperature. The mixture was heated at 60 0C for 0.2 hours. After cooling to room temperature, saturated NaHCO3 in water was added to the flask and the mixture was extracted with dichloromethane (3 x25 ml) and washed by brine, dried over sodium sulfate and concentrated. The resulting crude product was purified by Teledyne-Isco flash system by using DCM/MeOH, 0 to 15% of Methanol in dichloromethane to provide compound 30 as light yellow solids (155 mg, 32%). 1 H NMR (400 MHz, DMSO- d6) delta 12.66 (bs, I H), 10.37 (s, IH), 9.79 (s, IH), 7.797.06 (m, 7H1), 6.07 (bs, IH), 3.70 (m, 4H), 2.33 (m, 4H), 2.20 (s, 3H), 1.42 (m, I H), 0.85 (m, 4H) ; ESI-MS: calculated for (C25H27N9O2S) 517, found 518 (MH+). HPLC: retention time: 10.92 min. purity: 96%.
Reference： [1]Patent: WO2010/144550,2010,A1 .Location in patent: Page/Page column 76-77
  • 30
  • [ 17364-41-9 ]
  • [ 96799-02-9 ]
  • 4-([5-(furan-2-yl)-1H-pyrazol-3-yl]amino}methylidene)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one [ No CAS ]
Reference： [1]Bioorganic Chemistry,2011,vol. 39,p. 18 - 27
  • 31
  • [ 90771-00-9 ]
  • [ 96799-02-9 ]
  • C17H13N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With toluene-4-sulfonic acid; In ethanol; water; for 2h;Reflux; General procedure: A mixture of aldehyde (1.5 mmol), amine (3 mmol) and p-toluenesulphonic acid monohydrate (0.011 g, 0.06 mmol) in ethanol (10 mL) was heated to reflux for 2 h. After cooling, the precipitate was filtered off, washed with a little cold ethanol and dried in vacuo over anhydrous CaCl2.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4416 - 4421
  • 32
  • [ 17364-40-8 ]
  • [ 96799-02-9 ]
  • C23H17N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With toluene-4-sulfonic acid; In ethanol; water; for 2h;Reflux; General procedure: A mixture of aldehyde (1.5 mmol), amine (3 mmol) and p-toluenesulphonic acid monohydrate (0.011 g, 0.06 mmol) in ethanol (10 mL) was heated to reflux for 2 h. After cooling, the precipitate was filtered off, washed with a little cold ethanol and dried in vacuo over anhydrous CaCl2.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4416 - 4421
  • 33
  • [ 96799-02-9 ]
  • [ 1232220-74-4 ]
Reference： [1]Patent: US2011/294781,2011,A1
  • 34
  • [ 96799-02-9 ]
  • [ 1232223-78-7 ]
Reference： [1]Patent: US2011/294781,2011,A1
  • 35
  • [ 96799-02-9 ]
  • [ 105-53-3 ]
  • [ 1232223-75-4 ]
YieldReaction ConditionsOperation in experiment
20% There was dissolved, in ethanol (4 mL), 3-amino-5-furan-2-yl-pyrazole (502 mg, 3.35 mM) and then sodium ethoxide (2M ethanol solution, 4.19 mL, 8.38 mM) and diethyl malonate (610 muL, 4.02 mM) were added to the solution. This reaction liquid was stirred at 150 C. for 50 minutes under the irradiation with microwaves. This reaction mixture was filtered and the resulting solid was washed with diethyl ether. Phosphoryl chloride (20 mL) was added to the resulting solid with ice-cooling and then the resulting suspension was stirred for 8 hours, while refluxing the same with heating. The phosphoryl chloride was distilled off from this reaction liquid, ethanol was then added to the residue with ice-cooling and the mixture was stirred for 15 minutes. After the concentration of this reaction liquid, the resulting concentrate was purified by the silica gel column chromatography (methylene chloride) to thus give the title compound (167 mg, overall yield of these two steps: 20%). 1H-NMR (300 MHz, CDCl3): delta 6.56 (dd, 1H, J=1.8, 3.5 Hz), 6.91 (s, 1H), 6.95 (s, 1H), 7.02 (dd, 1H, J=0.6, 3.5 Hz), 7.58 (dd, 1H, J=0.6, 1.8 Hz); MS (ESI) m/z 254 (M+H)+.
Reference： [1]Patent: US2011/294781,2011,A1 .Location in patent: Page/Page column 33
  • 36
  • [ 96799-02-9 ]
  • C14H16N6O2 [ No CAS ]
Reference： [1]Patent: US2011/294781,2011,A1
  • 37
  • [ 796095-89-1 ]
  • [ 96799-02-9 ]
  • N4-[5-(2-furanyl)-1H-pyrazol-3-yl]-N2-[4-(methylsulfonyl)-2-morpholinyl]methyl}-6-(phenylmethyl)-2,4-pyrimidinediamine [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 948 - 952
  • 38
  • [ 796095-89-1 ]
  • [ 96799-02-9 ]
  • 6-benzyl-2-chloro-N-(5-(furan-2-yl)-1H-pyrazol-3-yl)pyrimidin-4-amine [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 948 - 952
  • 39
  • [ 96799-02-9 ]
  • 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
Reference： [1]Synthesis,2018,vol. 50,p. 1675 - 1686
  • 40
  • [ 96799-02-9 ]
  • 2-(furan-2-yl)-5-[N-(4-methoxybenzyl)amino]-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
Reference： [1]Synthesis,2018,vol. 50,p. 1675 - 1686
  • 41
  • [ 96799-02-9 ]
  • 2-(furan-2-yl)-5-morpholino-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
Reference： [1]Synthesis,2018,vol. 50,p. 1675 - 1686
  • 42
  • [ 79424-03-6 ]
  • [ 96799-02-9 ]
  • 2-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% General procedure: In a microwave vial, the 3-aminopyrazole 1 (1.0 mmol) was dissolved in 1,4-dioxane (4 mL). Ethyl 4,4,4-trifluoro-2-butynoate (2) (1.2mmol) was then added, and the mixture was degassed by bubbling with argon for 10 min. The sealed tube was heated at 110 C for 2 husing a microwave reactor. After cooling, MeONa (2.0 mmol) was added and the mixture was stirred for 12 h at r.t. The reaction mixture was neutralized with 10 mL of a solution of ethereal HCl (2 M) andthe solvent was removed under reduced pressure. The crude residue was purified using a silica gel column eluting with the mobile phases given below.
Reference： [1]Synthesis,2018,vol. 50,p. 1675 - 1686
  • 43
  • [ 1193-21-1 ]
  • [ 96799-02-9 ]
  • C11H8ClN5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 100℃; To a solution of 4,6-dichloro-pyrimidine (524 mg, 3.52 mmol) in iPrOH (18 mL) was added 5-Amino-3-(2-furyl)pyrazole (500 mg, 3.35 mmol) and N,N-diisopropylethylamine (0.88 ml, 5.03 mmol) at room temperature. The reaction was stirred at 100 C. for overnight. TLC was checked and the reaction was completed. The solvents were removed under reduced pressure. The crude product was purified by column chromatography (0-10% MeOH in DCM) to give compound 12 as yellow solids (333 mg, 38%). 1H NMR (400 MHz, DMSO-d6) delta 12.97 (s, 1H), 10.38 (br, 1H), 8.49 (s, 1H), 7.77 (s, 1H), 7.30 (br, 1H), 7.00-6.40 (m, 3H); ESI-MS: calcd for (C11H8ClN5O) 261, found 262 (MH+).
Reference： [1]Patent: US2018/346451,2018,A1 .Location in patent: Paragraph 0151-0152
  • 44
  • [ 96799-02-9 ]
  • C21H19FN6O [ No CAS ]
Reference： [1]Patent: US2018/346451,2018,A1
  • 45
  • [ 96799-02-9 ]
  • C21H19ClN6O [ No CAS ]
Reference： [1]Patent: US2018/346451,2018,A1
  • 46
  • [ 24424-99-5 ]
  • [ 96799-02-9 ]
  • tert-butyl 3-amino-5-(furan-2-yl)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% To a cold solution of <strong>[96799-02-9]5-amino-3-(2-furyl)pyrazole</strong> (1.00 g g, 6.70 mmol) in THF (20 ml) was added a suspension of sodium hydride (60% in mineral oil, 322 mg, 8.05 mmol) in THF (6 ml) at 0 C. slowly. After stirring at 0 C. for 30 minute, di-tert-butyldicarboxate (1.61 g, 7.38 mmol) was added. The mixture was stirred at 0 C. for 75 minutes. TLC was checked and the starting material was consumed. The reaction mixture was quenched with ice-water, extracted with ethyl acetate/Hexane (90/10, 25 ml x 2). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was triturated with EtOAc (5 ml)-Hexanes (30 ml). The yellow solids were collected by filtration, washed by hexanes to give compound 7 (1.41 g, 84% yield). 1H NMR (400 MHz, DMSO-d6) delta: 7.69 (m, 1H), 6.77 (m, 1H), 6.53 (m, 1H), 6.40 (br, 2H), 5.56 (s, 1H), 1.55 (s, 9H).
Reference： [1]Patent: US2018/346451,2018,A1 .Location in patent: Paragraph 0141-0142
  • 47
  • C13H10BrClN4S [ No CAS ]
  • [ 96799-02-9 ]
  • C20H16BrN7OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With triethylamine; In ethanol; at 20℃; for 5h; General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.
Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 418 - 422

Tags: 96799-02-9 synthesis path| 96799-02-9 SDS| 96799-02-9 COA| 96799-02-9 purity| 96799-02-9 application| 96799-02-9 NMR| 96799-02-9 COA| 96799-02-9 structure

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