14678-95-6|5-Amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid| Ambeed

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Quality Control of [ 14678-95-6 ] Purity: 95% SDS Specification

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Product Details of [ 14678-95-6 ]

CAS No. :	14678-95-6
Formula :	C₁₁H₁₁N₃O₃
M.W :	233.22
SMILES Code :	O=C(C1=C(N)N(C2=CC=C(OC)C=C2)N=C1)O
MDL No. :	MFCD00973939
InChI Key :	XOMCPZHFKFCRLB-UHFFFAOYSA-N
Pubchem ID :	3586349

Safety of [ 14678-95-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317
Precautionary Statements:	P280

Application In Synthesis of [ 14678-95-6 ]

* 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 [ 14678-95-6 ]

[ 14678-95-6 ] Synthesis Path-Downstream 1~22

2
(5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxamide) [ No CAS ]
[ 14678-95-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1.1 : 5-Amino-1-(4-methoxy-phenyϖ-1 H-pyrazole-4-carboxylic acid 5-Amino-1-(4-methoxy-phenyl)-1 H-pyrazole-4-carboxylic acid amide (2.0 g, 8.6 mmol) is heated to reflux in 30 ml of 8 M sodium hydroxide solution and 20 ml of ethanol for 18 hours. The reaction is acidified to pH 6, using 6 M HCI solution, and the formed precipitate is isolated by filtration and dried at the vacuum pump, yielding the title compound. HPLC: tR = 7.29 min; MS-ES: (M+H)+ = 234 ; TLC*: R, = 0.33.

References: [1]Patent: WO2008/52974,2008,A1 .Location in patent: Page/Page column 41.

3
[ 30069-31-9 ]
[ 14678-95-6 ]
[ 1023312-85-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 : 5-Amino-1-(4-methoxy-phenyl)-1 H-pyrazole-4-carboxylic acid [2-methyl-5-(3- trifluoromethyl-benzoylamino)-phenyl1-amide5-Amino-1-(4-methoxy-phenyl)-1 H-pyrazole-4-carboxylic acid (100 mg, 0.43 mmol), TPTU (140 mg, 0.47 mmol) and DIEA (184 ml, 1.07 mmol) are stirred at RT until complete formation of the intermediate activated ester. Then N-(3-amino-4-methyl-phenyl)-3-trifluoromethyl- benzamide (126 mg, 0.43 mmol) is added, and the mixture is heated to 9O0C for 3 hours, EPO <DP n="42"/>quenched by the addition of water and extracted using ethyl acetate. The product is purified by automated column chromatography and is dried at the high vacuum pump, yielding the title compound as a white solid. HPLC: tR = 10.57 min; MS-ES: (M+H)+ = 510 ; TLC*: Rf = 0.62.

References: [1]Patent: WO2008/52974,2008,A1 .Location in patent: Page/Page column 40-41.

4
[ 3471-32-7 ]
[ 14678-95-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

5
[ 15001-13-5 ]
[ 14678-95-6 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: Ethyl 5-amino-1-aryl-1H-pyrazole-4-carboxylates 7a-j(0.0017 mol), a solution of sodium hydroxide (3.5 mol.L-1, 2mL), and ethanol (99.5%, 20 mL) were added in a 50 mLround bottom flask and stirred, under reflux, for 17-54h. Thereaction was accompanied by means of TLC. After cooling,the pH was adjusted until 3 with HCl (8.4%). Afterwards, thesolution was poured into cold water. The solid obtained was filtered out and washed with cold water. After dry at room temperature, beige-coloured solids were obtained.
65%	With sodium hydroxide; In ethanol;Heating;	General procedure: 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid (3a)Ethanolic solution of NaOH (3 equivalents) was added to ethanolic solution of ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (1 equivalent) (2a). The reaction mixture was refluxed at 70C for 5-6 hours. Aqueous work up was done by adding reaction mixture in ice cold water and pH was made acidic. The white precipitate formed was filtered off and dried. Yield: 78%; Melting point: 191C; LC-ESI-MS (m/z): 204.2 (M+1)

References: [1]Letters in Organic Chemistry,2021,vol. 18,p. 335 - 343.
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

6
[ 14678-95-6 ]
5-(4-fluorophenyl)-1-(4-methoxyphenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

7
[ 14678-95-6 ]
1-(4-methoxyphenyl)-6-methyl-5-(pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

8
[ 14678-95-6 ]
1-(4-methoxyphenyl)-6-methyl-5-(4-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

9
[ 14678-95-6 ]
5-(5-bromopyridin-2-yl)-1-(4-methoxyphenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

10
[ 14678-95-6 ]
1-(4-methoxyphenyl)-6-methyl-5-(5-nitropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

11
[ 14678-95-6 ]
5-(4-(4-chlorophenyl)thiazol-2-yl)-1-(4-methoxyphenyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

12
[ 108-24-7 ]
[ 14678-95-6 ]
C₁₃H₁₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In tetrahydrofuran; at 70℃;	General procedure: 6-methyl-1-phenylpyrazolo[3,4-d][1,3]oxazin-4(1H)-one (4a)Acetic anhydride (6 equivalents) was added dropwise to a solution of 5-amino-1-phenyl-1H pyrazole-4-carboxylic acid (1 equivalent) in THF. The reaction was refluxed at 70 C for 7-8 hours. Work up was done by adding reaction mixture into an ice cold water and was stirred for 30-40 min. The precipitate formed was filtered off and dried. Yield: 55%; Melting point: 83C; LC-ESI-MS (m/z): 228.3 (M+1)

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4428 - 4433.

13
[ 14678-95-6 ]
[ 33760-73-5 ]
6-phenyl-8-(4-methoxyphenyl)-8,11-dihydropyrazolo[3',4':4,5]pyrimido[1,2-a][1,8]naphthyridin-11-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With N,N-dimethyl-formamide; In neat (no solvent); for 0.05833330000000001h;Microwave irradiation;	General procedure: A mixture of 3-aryl-2-chloro-1,8-naphthyridine 1 (0.01 mol), <strong>[14678-95-6]5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid</strong> 2 (0.01 mol) and DMF (5 drops) was subjected to MW irradiation at 400 watts intermittently at 30 s intervals for the period indicated in Table 2. On completion of the reaction (monitored by TLC), the reaction mixture was cooled and treated with cold water. The solid thus obtained was filtered, washed with water and purified by recrystallization from ethanol to give 3. 3a: IR(KBr) cm-1: 1656(C=O),1606(C=N); 1H NMR(CDCl3): δ 3.86(s,3H,OCH3), 7.80 (m, 2H, C3-H,C5-H), 7.86 (s, 1H, C10-H), 8.00 (m, 1H, C4-H), 8.75 (m, 1H,C2-H), 7.18-7.42 (m, 9H, Ar-H); MS (ESI):m/z 420 [M+H]+.