56367-24-9|5-Isopropyl-1H-pyrazol-3-amine| Ambeed

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Quality Control of [ 56367-24-9 ] Purity: 98% SDS Specification

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Product Details of [ 56367-24-9 ]

CAS No. :	56367-24-9
Formula :	C₆H₁₁N₃
M.W :	125.17
SMILES Code :	CC(C)C1=CC(N)=NN1
MDL No. :	MFCD08061035
InChI Key :	INSBBZDRQQVATI-UHFFFAOYSA-N
Pubchem ID :	2769527

Safety of [ 56367-24-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 56367-24-9 ]

* 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 [ 56367-24-9 ]

[ 56367-24-9 ] Synthesis Path-Downstream 1~35

2
[ 586-75-4 ]
[ 56367-24-9 ]
4-bromo-N-[1-(4-bromo-benzoyl)-5-isopropyl-1H-pyrazol-3-yl]-benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3367 - 3380.

3
[ 56367-24-9 ]
4-bromo-N-(5-isopropyl-1H-pyrazol-3-yl)-benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3367 - 3380.

4
[ 29509-06-6 ]
[ 56367-24-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine; In ethanol; at 20℃; for 3h;	A solution of 4-methyl-3-oxopentanenitrile (25 g, 225 mmol) and hydrazine (6.75 mL, 215 mmol) in ethanol (250 mL) was stirred at room temperature for 3 h, at which point LC/MS indicated exclusively product remained. The mixture was concentrated on a rotary evaporator followed by under high vacuum to give the desired product (27.8 g, 99%) as a yellow semisolid that was used without further purification.
99%	With hydrazine; In ethanol;	5-Isopropyl-1H-pyrazol-3-ylamine. A solution of 4-methyl-3-oxopentanenitrile (25 g, 225 mmol) and hydrazine (6.75 mL, 215 mmol) in ethanol (250 mL) was stirred at room temperature for 3 h, at which point LC/MS indicated exclusively product remained. The mixture was concentrated on a rotary evaporator followed by under high vacuum to give the desired product (27.8 g, 99%) as a yellow semisolid that was used without further purification.
59%	With hydrazine hydrate; In ethanol; at 0℃; for 4h;Reflux;	Step-2: Synthesis of 5-isopropyl-1H-pyrazol-3-amine, Compound (ii) To a solution of 4-methyl-3-oxopentanenitrile (15 g, 135 mmol) in EtOH (150 mL) was added hydrazine hydrate (7.30 g, 146 mmol) slowly at 0 C. The reaction mixture was heated to reflux for 4 h. Removal of EtOH under reduced pressure gave an oily residue that was dissolved in EtOAc (200 mL) and washed with freshly prepared brine (2*50 mL). The organic layer was dried over anhydrous sodium sulfate. Removal of EtOAc gave 5-isopropyl-1H-pyrazol-3-amine, Compound (ii) (10 g, 59% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 1.22 (d, 6H), 2.80-2.92 (m, 1H), 4.80 (brs, 3H), 5.41 (s, 1H).

	With hydrazine; In ethanol; at 70℃; for 12h;	A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.288 ml) and ethanol (45 ml) was heated at 700C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material <n="115"/>(0.574 g); 1H NMR: (DMSOd6) 1.13 (d, 6H), 2.76 (m, IH), 4.31 (br s, 2H), 5.17 (br s, IH), 11.05 (br s, IH); Mass Spectrum: M+H+ 126.
	With hydrazine; In ethanol; water; at 70℃; for 12h;	A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.288 ml) and ethanol (45 ml) was heated at 70 C. for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material (0.574 g); 1H NMR: (DMSOd6) 1.13 (d, 6H), 2.76 (m, 1H), 4.31 (br s, 2H), 5.17 (br s, 1H), 11.05 (br s, 1H); Mass Spectrum: M+H+ 126.
	With hydrazine; In ethanol; at 60℃; for 24h;	General procedure: A solution of 50 mg (0.34 mmol) of 3-oxo-3-phenylpropanenitrile and 11.6 mg (0.36 mmol) of hydrazine and 0.024 mL of acetic acid (0.37 mmol) in 3 mL of anhydrous ethanol was heated at 60 C for 24 hr. The mixture was cooled to ambient temperature and the solvent removed in vacuo. The residue was taken up in ethyl acetate, washed with saturated sodium bicarbonate. The organic layer was washed with brine and dried over MgSO4, filtered and evaporated. The solid residue waswashedwithethyl ether and dried in vacuo to give 45 mg (82%) of 3-phenyl-1H-pyrazol-5-amine.
	With hydrazine hydrate; In ethanol; at 0 - 70℃; for 3h;	General procedure: To a solution of 3-cyclopropyl-3-oxopropanenitrile (10 g, 91.7 mmol)) in ethanol (200 mL) was dropwise added hydrazine monohydrate (7.74 mL, 160 mmol) at 0 . The resulting mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated.

References: [1]Patent: US2008/249079,2008,A1 .Location in patent: Page/Page column 144.
[2]Patent: US2009/232828,2009,A1 .
[3]Patent: US2014/179668,2014,A1 .Location in patent: Paragraph 0832.
[4]Patent: WO2007/99317,2007,A1 .Location in patent: Page/Page column 113-114.
[5]Patent: US2009/76075,2009,A1 .Location in patent: Page/Page column 49.
[6]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3736 - 3740.
[7]Bulletin of the Korean Chemical Society,2020,vol. 41,p. 567 - 569.

5
[ 3764-01-0 ]
[ 56367-24-9 ]
[ 71-36-3 ]
[ 898281-45-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In ethyl acetate;	2,6-Dichloropyrimidin-4-yl-(5-isopropyl-1H-pyrazol-3-yl)-amine. A mixture of 2,4,6-trichloropyrimidine (1.8 g, 9.8 mmol), 5-isopropyl-1H-pyrazol-3-ylamine (1.25 g, 10.0 mmol), diisopropylethylamine (3 mL, 18 mmol) and 1-butanol (10 mL) was heated to 80 C. for 2 h, at which point LC/MS indicated that the reaction was complete. The solvents were removed on a rotary evaporator and the paste was treated with ethyl acetate. The organic solution was washed with water and brine and dried over magnesium sulfate. The residue was concentrated on a rotary evaporator, and the pale yellow solid that remained was purified via flash chromatography to yield the desired product (2.3 g, 70%) as an off white solid.

References: [1]Patent: US2009/232828,2009,A1 .

6
[ 3764-01-0 ]
[ 56367-24-9 ]
[ 898281-45-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 80℃; for 2h;	A mixture of 2,4,6-trichloropyrimidine (1.8 g, 9.8 mmol), 5-isopropyl-1H-pyrazol-3-ylamine (1.25 g, 10.0 mmol), diisopropylethylamine (3 mL, 18 mmol) and 1-butanol (10 mL) was heated to 80 C. for 2 h, at which point LC/MS indicated that the reaction was complete. The solvents were removed on a rotary evaporator and the paste was treated with ethyl acetate. The organic solution was washed with water and brine and dried over magnesium sulfate. The residue was concentrated on a rotary evaporator, and the pale yellow solid that remained was purified via flash chromatography to yield the desired product (2.3 g, 70%) as an off white solid.

References: [1]Patent: US2008/249079,2008,A1 .Location in patent: Page/Page column 144.

7
[ 947763-38-4 ]
[ 56367-24-9 ]
[ 947764-04-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20 - 80℃; for 13h;	EXAMPLE 7 N-(5-isopropylpyrazol-3-yl)-2-[5-(6-fluoroquinolin-4-yloxy)-3-methoxypyridin-2-yl]acetamide 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.437 g) and 2-hydroxypyridine N-oxide (0.253 g) were added in turn to a stirred mixture of 2-[5-(6-fluoroquinolin-4-yloxy)-3-methoxypyridin-2-yl]acetic acid (0.25 g), <strong>[56367-24-9]3-amino-5-isopropylpyrazole</strong> (0.162 g), diisopropylethylamine (0.4 ml) and NMP (1.7 ml). The resultant mixture was stirred at ambient temperature for 7 hours and subsequently heated to 80 C. for 6 hours. The mixture was evaporated and the residue was purified by preparative HPLC using a Waters 'Xterra' reversed-phase column (5 microns silica, 30 mm diameter, 150 mm length) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.047 g); 1H NMR: (DMSOd6) 1.19 (d, 6H), 3.81 (s, 3H), 3.84 (s, 2H), 6.27 (s, 1H), 6.75 (d, 1H), 7.53 (d, 1H), 7.77 (m, 1H), 8.01 (m, 1H), 8.13 (m, 2H), 8.72 (d, 1H), 10.42 (br s, 1H), 12.0 (br s, 1H); Mass Spectrum: M+H+ 436.

References: [1]Patent: US2009/76075,2009,A1 .Location in patent: Page/Page column 48-49.

8
[ 109-01-3 ]
[ 108-77-0 ]
[ 639090-54-3 ]
[ 56367-24-9 ]
[ 1258423-74-3 ]

Yield	Reaction Conditions	Operation in experiment
37%		To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 niL) was added 2-amino-5-isopropylpyrazole (263 mg, 1.63 mmol) and DIPEA (0.28 niL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. Then, 1 -methylpiperazine (0.18 mL, 1.63 mmol) and DIPEA (0.28 mL, 1.90 mmol) were added to the above mixture and allowed to stir at room temperature for 3 hours. Next, compound (1) (628 mg, 3.25 mmol) and DIPEA (0.57 mL, 2.25 mmol) were added to the mixture and 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 56 as light yellow solid (110 mg, 37 %). IH NMR (400 MHz, DMSO-d6) δ 11.77 (bs, IH, NH), 10.42 (s, IH, NH), 9.50 (bs, IH, NH), 7.73 (bs, 2H, Ar-H), 7.48 (d, J = 8.4 Hz, 2H, Ar-H), 5.40 (bs,lH, Ar-H), 3.68 (bs, 4H, 2CH2), 2.33 (bs, 4H, 2CH2), 2.21 (s, 3H, CH3), 1.83-1.81 (m, IH, CH), 1.24 (bs, 3H, CH3), 1.05 (bs, 3H, CH3),0.84-0.82 (m, 4H, Ar-H); ESI-MS: calcd for (C24H31N9OS) 493, found 494 [M+H]+. HPLC: retention time: 15.38 min. purity: 99%.

References: [1]Patent: WO2010/144359,2010,A1 .Location in patent: Page/Page column 101.

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[ 4981-63-9 ]
[ 56367-24-9 ]
[ 1403758-06-4 ]