59844-05-2|3-(2-Nitrophenyl)-1H-pyrazole| Ambeed

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Quality Control of [ 59844-05-2 ] Purity: 95% SDS Specification

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Product Details of [ 59844-05-2 ]

CAS No. :	59844-05-2
Formula :	C₉H₇N₃O₂
M.W :	189.17
SMILES Code :	[O-][N+](=O)C1=C(C=CC=C1)C1=NNC=C1
MDL No. :	MFCD00665858
InChI Key :	LNRBQCSTNUDDGL-UHFFFAOYSA-N
Pubchem ID :	2737069

Safety of [ 59844-05-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 59844-05-2 ]

* 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 [ 59844-05-2 ]

[ 59844-05-2 ] Synthesis Path-Downstream 1~26

1
[ 59844-05-2 ]
[ 111562-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	palladium; In methanol;	a) 2-(1H-Pyrazol-3-yl)-phenylamine To <strong>[59844-05-2]3-(2-nitrophenyl)-1H-pyrazole</strong> (Butt Park Ltd.) (100 mg, 0.53 mmol) was added methanol (10 mL) and the solution was degassed under Ar. To this solution was added 10% palladium on carbon (100 mg) and the mixture stirred at RT for 50 min under hydrogen (1 atm). The mixture was filtered through a short column of Celite, the product was washed off the column with methanol, and the solvent removed in vacuo to yield the title compound as a colorless crystalline solid (84 mg, quantitative yield). 1H-NMR (CDCl3; 400 MHz): δ 7.55 (d, 1H, J=2.3 Hz), 7.51 (m, 1H), 7.14 (m, 1H), 7.79-6.75 (m, 2H), 6.62 (m, 1H, J=2.4). LC-MS (ESI, m/z): Calcd. for C9H10N3: 160.1 (M+H); found: 160.1.
	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2585.81 Torr;	A mixture of compound 3 (25 g, 0.13 mol) and Pd/C (5 g, 10% w/w) in MeOH (500 mL) was stirred at room temperature under H2 (50 psi) overnight. After filtration, the filtrate was concentrated under vacuum to give compound 4 (17 g, yield: 81 %), which was used to the next step without further purification.

References: [1]Patent: US2005/113566,2005,A1 .
[2]Patent: WO2012/7006,2012,A1 .Location in patent: Page/Page column 33.

3
[ 1072-63-5 ]
[ 59844-05-2 ]

Yield	Reaction Conditions	Operation in experiment
40%		The aldehyde 1 (1.5 mmol) was added to a solution of p-Toluenesulfonyl hydrazide (1.5 mmol) in acetonitrile (250 mL). After the mixture was stirred for 3 h at room temperature, a solution of 5 N NaOH (1.5 mmol) was added and the mixture was stirred for a further 20 min. The N-vinylimidazole (7.5 mmol) was added, and the mixture was stirred at 50 C. for 2 days. The volatiles were evaporated under reduced pressure, and the residue was dissolved in a 1:1 mixture of H2O-EtOAc (70 mL). The organic layer was separated and dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude material was purified by flash chromatography on silica gel to give pure product 2 in 40% yield. 1H NMR: δ 7.71 (d, J=8 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 7.59 (d, J=2.5 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 7.47 (t, J=7.5 Hz, 1H), 6.47 (d, J=2.5 Hz, 1H). LC-MS: (4.01 min, m/z, ES+): calcd: 189.05; Found: 190.08.

References: [1]Patent: US2006/183751,2006,A1 .Location in patent: Page/Page column 82.

4
[ 59844-05-2 ]
[ 59844-06-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 38 N,N,α-Trimethyl-<strong>[59844-05-2]3-(o-nitrophenyl)pyrazole</strong>-1-acetamide Following the procedure of Example 1, but substituting <strong>[59844-05-2]3-(o-nitrophenyl)pyrazole</strong> for 4-methyl-3-phenylpyrazole there was obtained N,N,α-trimethyl-<strong>[59844-05-2]3-(o-nitrophenyl)pyrazole</strong>-1-acetamide, as a brown liquid.

References: [1]Patent: US4072498,1978,A .

5
[ 87488-61-7 ]
[ 59844-05-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrazine hydrate; In ethanol;	The intermediate 1 (114 mg, 0.6 mmol) with ethanol mixed solvent, with the addition of about two equivalents of hydrazine hydrate, stirring the reaction from a few hours to intermediate 1 disappears. Cooling, to evaporate the solvent, get 90 mg intermediate 2, yield 90%,
87%	With hydrazine hydrate; at 100℃; for 10h;	Compounds13a-d were synthesized as reported in the literature [14,15]. A so-lution of commercially available 2-nitroacetophenone and N,N-dimethylformamide dimethyl acetal in DMF was heated at 100Cfor 2 h. The reaction mixture was concentrated and the resultantsolid was washed with Et2O and collected by ltration to afford10a. 10a and hydrazine monohydrate in ethanol was reuxed for10 h. The mixture was concentrated and the resultant was sub-jected to column chlomatography on silica gel to give 11a. 2-nitrobenzamide was dissolved in dimethylformamide dimethyla-cetal and heated to 100C for 1 h. The reaction mixture was cooledand a white precipitate was collected by ltration and rinsed withhexane to provide 10b. 10b in acetic acid and n-butanol was treatedwith hydrazine monohydrate, and heated to reux for 2 h. Thesolvent was removed in vacuo, and the residue was subjected tocolumn chlomatography on silica gel to give 11b. 13a-b could beobtained through methylation and reduction. A cooper-catalizedcoupling was used to synthesize 12c and 12d and followed by areduction, 13c and 13d were obtained in good yields. Condensationof commercially available 2,4-dichloropyrimidine with 13a-d in 2-BuOH containing DIPEA provided intermediates with structure15a-d. 4-methylbenzenesulfonic acid hydrate was added in oneportion to 15 and 4-uoro-2-methoxy-5-nitroaniline in 2-pentanol.The resulting mixture was stirred at 105C for 2.5 h. The mixturewas cooled to room temperature. The precipitate was collected byltration, washed with 2-pentanol, and dried under vacuum toafford 16a-16d as a yellow solid, which were used in the subse-quent reaction without purication.
	With hydrazine; In ethanol;Reflux;	To a solution of compound 2 (20 g, 0.09 mol) in absolute ethanol (168 mL) was added H2NNH2 (4.3 g, 0.133 mol). After the addition was completed, the mixture was stirred at reflux overnight. The resulting mixture was concentrated under vacuum. The residue was washed with water (50 mL) and dried under vacuum to give compound 3 (15.1 g, yield: 88%), which was used to the next step without further purification. 1H NMR (CDCI3 300MHz TMS): 57.74-7.70 (m, 2H), 7.64-7.57 (m, 2H), 7.50-7.45 (m, 1 H), 6.53-6.51 (m, 1 H), 6.1 1 (brs, 1 H).

References: [1]Patent: CN107098887,2017,A .Location in patent: Paragraph 0029; 0034; 0035.
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.
[3]Patent: WO2012/7006,2012,A1 .Location in patent: Page/Page column 32; 33.

6
[ 59844-05-2 ]
[ 30131-67-0 ]

References: [1]Patent: WO2012/7006,2012,A1 .

7
[ 577-59-3 ]
[ 59844-05-2 ]

References: [1]Patent: WO2012/7006,2012,A1 .
[2]Patent: CN107098887,2017,A .
[3]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

8
[ 59844-05-2 ]
N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-((2-(1-methyl-1H-pyrazole-3-yl)phenyl)amino)pyrimidine-2-yl)amino)phenyl)acrylamide [ No CAS ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

9
[ 59844-05-2 ]
[ 87488-80-0 ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

10
[ 59844-05-2 ]
C₁₄H₁₂ClN₅ [ No CAS ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

11
[ 59844-05-2 ]
C₂₁H₁₈FN₇O₃ [ No CAS ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

12
[ 59844-05-2 ]
N2-(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)-N4-(2-(1-methyl-1H-pyrazol-3-yl)phenyl)pyrimidine-2,4-diamine [ No CAS ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

13
[ 59844-05-2 ]
N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-((2-(1-methyl-1H-pyrazole-3-yl)phenyl)amino)pyrimidine-2-yl)phenyl-1,2,4-triazole [ No CAS ]

References: [1]Patent: CN107098887,2017,A .
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.

14
[ 59844-05-2 ]
[ 74-88-4 ]
[ 305811-47-6 ]

Yield	Reaction Conditions	Operation in experiment
62%		The intermediate 2 (90 mg, 0.5 mmol) dissolved in THF, ice is added under the condition of NaH (40 mg, 1 mmol), stirring one hour after adding methyl iodide (31 Ul, 0.5 MMOL). Stir at room temperature reaction from a few hours to intermediate 2 disappear, concentrated reaction system, column chromatography, shall be 168 mg intermediate 3, yield 62%.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 298 - 306.
[2]Patent: CN107098887,2017,A .Location in patent: Paragraph 0029; 0036; 0037.

15
[ 59844-05-2 ]
N-(2-(2-(dimethylamino)ethoxy)-4-methoxy-5-((4-((2-(1-methyl-1H-pyrazole-3-yl)phenyl)amino)pyrimidine-2-yl)amino)phenyl)acrylamide [ No CAS ]