[ CAS No. 50920-65-5 ] {[proInfo.proName]}

Name: 50920-65-5|1-Ethyl-3-methyl-1H-pyrazole-5-carboxylic acid|97%
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SKU: A139361
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Quality Control of [ 50920-65-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 50920-65-5 ]

Product Details of [ 50920-65-5 ]

CAS No. :	50920-65-5	MDL No. :	MFCD00156147
Formula :	C₇H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VFMGOJUUTAPPDA-UHFFFAOYSA-N
M.W :	154.17	Pubchem ID :	2743794
Synonyms :

Calculated chemistry of [ 50920-65-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.43
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.22
TPSA :	55.12 Å²

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) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	0.79
Log Po/w (WLOGP) :	0.91
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	0.46
Consensus Log Po/w :	0.79

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.5
Solubility :	4.9 mg/ml ; 0.0318 mol/l
Class :	Very soluble
Log S (Ali) :	-1.53
Solubility :	4.57 mg/ml ; 0.0296 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.95
Solubility :	17.4 mg/ml ; 0.113 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 50920-65-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 50920-65-5 ]

* 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 [ 50920-65-5 ]
Downstream synthetic route of [ 50920-65-5 ]

[ 50920-65-5 ] Synthesis Path-Upstream 1~4

1
[ 50920-64-4 ]
[ 50920-65-5 ]

Reference： [1] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 870 - 878
[2] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1121 - 1128
[3] Chemical Papers, 2017, vol. 71, # 11, p. 2053 - 2061

2
[ 615-79-2 ]
[ 50920-65-5 ]

Reference： [1] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 870 - 878
[2] Chemical Papers, 2017, vol. 71, # 11, p. 2053 - 2061

3
[ 4027-57-0 ]
[ 50920-65-5 ]

Reference： [1] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 870 - 878

4
[ 50920-65-5 ]
[ 64-17-5 ]
[ 50920-64-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2 h; Inert atmosphere Stage #2: at 20℃; for 1 h;	Oxalyl chloride (5.68 ml, 64.9 mmol) was added to a suspension of l-ethyl-3-methyl- lH-pyrazole-5-carboxylic acid (5 g, 32.4 mmol) in DCM (40 mL) at RT under l\h and two drops of DMF were added. The mixture was stirred for 2 hours at RT, concentrated and dried in vacuo. Ethanol (50 ml, 856 mmol) was added, and the mixture was stirred for 1 hour at RT. The reaction was concentrated and dried in vacuo .o give a light-yellow oil which was taken into EtOAc (100 mL), washed with saturated NaHC03 and brine, dried over Na2S0 , filtered, concentrated and the resulting residue was dried in vacuoto give the title compound (5.5 g, 30.2 mmol, 93 percent yield) as a light-yellow oil. *H NMR (400 MHz, CHLOROFORM-tf) δ ppm 6.63 (s, 1 H) 4.56 (q, 7=7.11 Hz, 2 H) 4.35 (q, 7=7.11 Hz, 2 H) 2.30 (s, 3 H) 1.44 (t, 7=7.28 Hz, 3 H) 1.39 (t, 7=7.28 Hz, 3 H). LCMS (LCMS Method E): Rt = 0.81 min, [M+H]⁺ = 183.1.

Reference： [1] Patent: WO2017/175147, 2017, A1, . Location in patent: Page/Page column 191

[ 50920-65-5 ] Synthesis Path-Downstream 1~2

1
[ 50920-65-5 ]
[ 128249-59-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 120℃; Cooling with ice;	2.1 Step 1: Synthesis of 1-ethyl-3-methyl-1H-pyrazole-5-carbonyl chloride Disperse 1-ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (4g, 25.9mmol) in dry DCM (80mL),Under an ice bath, oxalyl chloride (3.9 g, 31.1 mmol) and a catalytic amount of DMF were added dropwise thereto.After reacting for 1 hour at room temperature, the volatiles were removed by rotary evaporation under reduced pressure.DCM (20mL) was added to the crude product, and the solvent was removed by rotary evaporation to obtain1-Ethyl-3-methyl-1H-pyrazole-5-carbonyl chloride (4.46g, 100% yield) was directly used in the next reaction.
100%	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20 - 30℃; for 1h; Inert atmosphere;	3. Intermediate compound: Synthesis of 1-ethyl-3-methyl-1H-pyrazole-5-carbonyl isothiocyanate 1-Ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (4.00 g, 25.9 mmol) was dispersed in dry DCM (80 mL), to which was added oxalyl chloride (3.9 g, 31.1 mmol) and a catalytic amount of DMF. After reacting for 1 hour at room temperature, the volatiles were removed by rotary evaporation under reduced pressure. DCM (20 mL) was added to the crude product, and the solvent was removed by rotary evaporation to obtain 1-ethyl-3-methyl-1H-pyrazole-5-carbonyl chloride (4.46 g, 100% yield), which was used directly for the next reaction.
	With dichlorosulfoxide at 79℃; for 2h;	1.3; 7.3; 14.3; 15.5; 69.1 Step 3: 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide.; A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.802 g, 4.67 mmol) and thionyl chloride (10 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by distillation. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (0.905 g, 3.59 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 2 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford the pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (1.05 g, 2.73 mmol, 76%).; Step 3: 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide.; A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.608 mg, 3.53 mmol) and thionyl chloride (10 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by distillation. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 5-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (0.685 g, 2.72 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 2 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (0.760 g, 1.96 mmol, 72%).; Step 3: 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide.; A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.168 g, 1.09 mmol) and thionyl chloride (4 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by distillation. The crude acid chloride was cooled to 65° C., and then dissolved in THF (5 mL). 5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one (0.200 g, 0.840 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. Subsequently, the reaction mixture was allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a pale yellow precipitate. The pale yellow solids were filtered to afford the pure product (0.141 g, 0.377 mmol, 34.5%).; Step 5: 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide.; A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.887 g, 5.16 mmol) and thionyl chloride (5 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride then was removed by concentration in vacuo. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (1.00 g, 3.97 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 4 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a precipitate. The solids were filtered to afford the pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.741 g, 1.94 mmol, 49%).; The 2-Ethyl-5-ethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide was prepared from 3-nitrobenzoyl chloride using the following multiple step procedure: Step 1: 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide.; A dry 25 mL flask was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (0.891 g, 5.16 mmol) and thionyl chloride (15 mL) and allowed to stir at 79° C. for 2 h. The thionyl chloride was then removed by concentration in vacuo. The crude acid chloride was cooled to room temperature, and then dissolved in THF (5 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 1.0 g, 3.97 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The tan solids were filtered to afford the pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (1.354 g, 3.49 mmol, 88%).

	With dichlorosulfoxide In 1,2-dichloro-ethane for 4h; Reflux;
	With dichlorosulfoxide In 1,2-dichloro-ethane for 2h; Reflux;	Synthesis of 1,3-dimethyl-1H-pyrazole acyl chloride (4a) and its analogues (4b-p) General procedure: 3a (0.01 mol) and thionyl chloride (2.95 g, 0.025 mol) were successively added to 15 ml 1,2-dichloroethane. After 2 h under reflux, the solvent was removed under reduced pressure. 4a was obtained and without further purification and calculating the yield, next reaction was carried out immediately. The analogues 4b-p were prepared in a similar procedure.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	To a 1L round bottom flask was added l-ethyl-3-methyl-lH-pyrazole-5-carboxylic acid (25 g, 162 mmol) and DCM (500 mL). To this heterogeneous solution was added DMF (0.1 mL, 1.291 mmol) followed by the slow addition of oxalyl chloride (15.61 mL, 178 mmol). During the addition, bubbling was noticed. After stirring for 1 hr at room temperature, the volatiles were removed under vacuum and the crude was co-evaporated twice with dichloromethane (100 mL each). It was assumed 100% yield and the crude (l-ethyl-3-methyl-lH-pyrazole-5- carbonyl chloride (28.0 g, 162 mmol, 100 % yield)) was used directly as it is in the next reaction.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	1-ethyl-3-methyl-1 H-pyrazole-5-carbonyl isoth iocyanate0 To a 1L round bottom flask was added 1-ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (25 g, 162 mmol) and DCM (500 mL). To this heterogeneous mixture was added DMF (0.1 mL,1.291 mmol) followed by the slow addition of oxalyl chloride (15.61 mL, 178 mmol). During the addition, bubbling was noticed. After stirring for 1 hr at room temperature, the volatiles were removed under vacuum and the crude was co-evaporated twice with dichloromethane (100 mL each). It was assumed 100% yield and the crude (1-ethyl-3-methyl-1H-pyrazole-5-carbonyl chloride (28.0 g, 162 mmol, 100 % yield)) was used directly as it is in the next reaction.
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h;	5 Intermediate 5 To a 1L round bottom flask was added l-ethyl-3-methyl-lH-pyrazole-5-carboxylic acid (25 g, 162 mmol) and DCM (500 mL). To this heterogeneous solution was added DMF (0.1 mL, 1.291 mmol) followed by the slow addition of oxalyl chloride (15.61 mL, 178 mmol). During the addition, bubbling was noticed. After stirring for 1 hr at room temperature, the volatiles were removed under vacuum and the crude was co-evaporated twice with dichloromethane (100 mL each). It was assumed 100% yield and the crude (1- ethyl-3-methyl-lH-pyrazole-5-carbonyl chloride (28.0 g, 162 mmol, 100 % yield)) was used directly as it is in the next reaction.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	Intermediate 51-ethyl-3-methyl-1H-pyrazole-5-carbonyl isothiocyanate To a 1L round bottom flask was added 1-ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (25 g, 162 mmol) and DCM (500 mL). To this heterogeneous solution was added DMF (0.1 mL, 1.291 mmol) followed by the slow addition of oxalyl chloride (15.61 mL, 178 mmol). Duringthe addition, bubbling was noticed. After stirring for 1 hr at room temperature, the volatiles were removed under vacuum and the crude was co-evaporated twice with dichloromethane (100 mL each). It was assumed 100% yield and the crude (1-ethyl-3-methyl-1H-pyrazole-5- carbonyl chloride (28.0 g, 162 mmol, 100 % yield)) was used directly as it is in the next reaction.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	To a 1L round bottom flask was added 1-ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (25 g, 162 mmol) and DCM (500 mL). To this heterogeneous solution was added DMF (0.1 mL, 1.291 mmol) followed by the slow addition of oxalyl chloride (15.61 mL, 178 mmol). After stirring for 1 h at room temperature, the volatiles were removed under vacuum and the crude was co-evaporated twice with dichloromethane (100 mL each). It was assumed 100% yield and the crude (1-ethyl-3-methyl-1H-pyrazole-5-carbonyl chloride (28.0 g, 162 mmol, 100% yield)) was used directly.
17.8 g	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Inert atmosphere;	1 -Ethyl-3-methyl-1 H-pyrazole-5-carbonyl chloride To a suspension of 1 -ethyl-3-methyl-1 /-/-pyrazole-5-carboxylic acid (14.7 g, 95 mmol) in dichloromethane (DCM) (300 ml_) under an atmosphere of N2 was added A/,A/-dimethylformamide (0.185 ml_, 2.38 mmol), followed by oxalyl chloride (9.18 ml_, 105 mmol) dropwise. The mixture was stirred at RT for 2 h. Following this duration, the mixture was concentrated to dryness and the crude title compound (17.18 g) was carried forward without any further purification.
2.23 g	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice;	2.1 Example 2: Synthesis of T-1 Step 1: Disperse 1-ethyl-3-methyl-1H-pyrazole-5-carboxylic acid (CAS: 50920-65-5) (2.00 g, 12.9 mmol) in dry DCM (40 mL) and place it on ice Under the bath, oxalyl chloride (1.9 g, 15.6 mmol) and a catalytic amount of DMF were added dropwise thereto.After reacting at room temperature for 1 h, the solvent and excess oxalyl chloride were removed by rotary evaporation under reduced pressure to obtain T-1-1 (2.23 g).
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 15℃; for 1h;	1.8; 5.1 Step 8: Preparation of compound 1-11 Compound 1-10 (1 g, 6.49 mmol) was dissolved in dichloromethane (20 mL), N,N-dimethylformamide (0.1 mL) and oxalyl chloride (906 mg, 7.14 mmol, 624 L) were serially added, and the reaction system was stirred at 15 °C for 1 h and concentrated under reduced pressure to obtain a crude product 1-11 which was used in the next step directly without further purification.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 15℃; for 1h;	1.8; 5.1 Step 8: Preparation of compound 1-11 Compound 1-10 (1 g, 6.49 mmol) was dissolved in dichloromethane (20 mL), N,N-dimethylformamide (0.1 mL) and oxalyl chloride (906 mg, 7.14 mmol, 624 L) were serially added, and the reaction system was stirred at 15 °C for 1 h and concentrated under reduced pressure to obtain a crude product 1-11 which was used in the next step directly without further purification.

Reference： [1]Current Patent Assignee: CHENGDU HITGEN PHARMACEUTICAL DEV; CHENGDU PIONEER PHARMACEUTICAL DEVELOPMENT CO LTD - CN111471056, 2020, A Location in patent: Paragraph 0202-0205
[2]Current Patent Assignee: CHENGDU PIONEER PHARMACEUTICAL DEVELOPMENT CO LTD - EP3919488, 2021, A1 Location in patent: Paragraph 0059; 0063; 0075-0076
[3]Current Patent Assignee: ABBVIE INC - US2007/32478, 2007, A1 Location in patent: Page/Page column 65; 67-70; 81
[4]Huang, Danling; Huang, Mingzhi; Liu, Aiping; Liu, Xingping; Liu, Weidong; Chen, Xiaoyang; Xue, Hansong; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1121 - 1128]
[5]Huang, Danling; Huang, Mingzhi; Liu, Weidong; Liu, Aiping; Liu, Xingping; Chen, Xiaoyang; Pei, Hui; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang [Chemical Papers, 2017, vol. 71, # 11, p. 2053 - 2061]
[6]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/175147, 2017, A1 Location in patent: Page/Page column 185
[7]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/175156, 2017, A1 Location in patent: Page/Page column 99; 100
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2019/69275, 2019, A1 Location in patent: Page/Page column 62-63
[9]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2019/69269, 2019, A1 Location in patent: Page/Page column 202
[10]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2019/69270, 2019, A1 Location in patent: Page/Page column 153; 154
[11]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2020/202091, 2020, A1 Location in patent: Paragraph 00176-00177
[12]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN112940004, 2021, A Location in patent: Paragraph 0119-0121
[13]Baek, Soo Yeon; Han, Soo Bong; Jeon, Min Jae; Jo, Seongman; Jung, Hee Ra; Kang, Miso; Kim, Hyejin; Kim, Nam-Jung; Lee, Donghee; Lee, Hyelim; Lee, Jeehee; Lee, Joo-Youn; Lee, Sanghee [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5407 - 5432]
[14]Current Patent Assignee: SHANGHAI JEMINCARE PHARMACEUTICALS; JIANGXI JEMINCARE GROUP CO LTD - EP4006024, 2022, A1 Location in patent: Paragraph 0102-0103; 0219-0222
[15]Current Patent Assignee: SHANGHAI JEMINCARE PHARMACEUTICALS; JIANGXI JEMINCARE GROUP CO LTD - EP4006024, 2022, A1 Location in patent: Paragraph 0102-0103; 0219-0222

2
[ 74-96-4 ]
[ 25016-17-5 ]
[ 50920-46-2 ]
[ 50920-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; In water; dimethyl sulfoxide; at 20.0℃;	Methyl 5-methylpyrazole-3-carboxylate (14 g, 0.1 mol), ethyl bromide (10.9 g, 0.1 mol),Tetrabutylammonium hydrogen sulfate (2.7 g, 0.008 mol), dissolved in 10 ml of dimethyl sulfoxide (DMSO),Potassium hydroxide solution was added dropwise [potassium hydroxide solution: a solution obtained by dissolving 22.4 g (0.40 mol) of potassium hydroxide in 20 ml of water],The reaction is exothermic, the addition is completed, and the mixture is stirred at room temperature overnight, diluted with water and quenched to adjust the pH to 2 to precipitate a white solid.Nuclear magnetic resonance test is a mixture of 1-ethyl-3-methylpyrazole-5-carboxylic acid and 1-ethyl-5-methylpyrazole-3-carboxylic acid.The ratio is 1:1, and the total weight of the product after drying is 14.6 g, and the yield is 94.8percent.

Reference： [1]Patent: CN108863936,2018,A .Location in patent: Paragraph 0027; 0028; 0029

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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 50920-65-5 ] {[proInfo.proName]}

Quality Control of [ 50920-65-5 ]

Related Doc. of [ 50920-65-5 ]

Product Details of [ 50920-65-5 ]

Calculated chemistry of [ 50920-65-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 50920-65-5 ]

Application In Synthesis of [ 50920-65-5 ]

[ 50920-65-5 ] Synthesis Path-Upstream 1~4

[ 50920-65-5 ] Synthesis Path-Downstream 1~2

Related Functional Groups of [ 50920-65-5 ]

Carboxylic Acids

Related Parent Nucleus of [ 50920-65-5 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 50920-65-5 ]

Related Parent Nucleus of
[ 50920-65-5 ]