[ CAS No. 90390-33-3 ] {[proInfo.proName]}

Name: 90390-33-3|3-Chloro-5-fluorobenzylamine|95%
Brand: Ambeed
SKU: A272558
Rating: 93 (32 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 90390-33-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 90390-33-3 ]

Product Details of [ 90390-33-3 ]

CAS No. :	90390-33-3	MDL No. :	MFCD06213787
Formula :	C₇H₇ClFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XJCYOVBALKWQQC-UHFFFAOYSA-N
M.W :	159.59	Pubchem ID :	457616
Synonyms :

Calculated chemistry of [ 90390-33-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.08
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.51
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	2.57
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	2.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.11 mg/ml ; 0.00694 mol/l
Class :	Soluble
Log S (Ali) :	-1.66
Solubility :	3.46 mg/ml ; 0.0216 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.0753 mg/ml ; 0.000472 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 90390-33-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 90390-33-3 ]

* 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 [ 90390-33-3 ]

[ 90390-33-3 ] Synthesis Path-Downstream 1~33

1
3-Chloro-5-fluoro-benzaldehyde oxime [ No CAS ]
[ 90390-33-3 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1111 - 1118

2
[ 5714-17-0 ]
[ 90390-33-3 ]
[ 1422955-17-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1739 - 1747

3
3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid [ No CAS ]
[ 90390-33-3 ]
3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 4.0h;Inert atmosphere;	3-Chloro-5-fluorobenzylamine (97 mg, 0.61 mmol) and Et3N (0.24 ml, 1.8 mmol) followed by T3P (0.6 ml, 1.8 mmol) are added at 0 C. to a solution of 3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (150 mg, 0.61 mmol) in 5 ml of dichloromethane. The reaction mixture is stirred at room temperature under nitrogen for 4 hours. When the reaction is complete, water is added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are subsequently washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation, the residue is purified by chromatography on silica gel, giving the product as colourless solid (150 mg, 63% yield); Thin-layer chromatogram: chloroform/methanol=9.5:0.5), Rf: 0.3 LC/MS: 388.1 (M+H at 1. 388 min); HPLC: Rt 5.12 min (HPLC purity 95.15%, 95.46%); 1H NMR (DMSO-d6, 400 MHz): delta [ppm] 9.13 (t, J=6.08 Hz, 1H), 7.70-7.68 (m, 2H), 7.43 (t, J=8.64 Hz, 2H), 7.32-7.29 (m, 1H), 7.24-7.20 (m, 2H), 7.09 (d, J=9.80 Hz, 1H), 4.42-4.34 (m, 2H), 3.95-3.89 (m, 2H), 2.61-2.58 (m, 1H), 2.28-2.22 (m, 1H).

Reference： [1]Patent: US2013/296274,2013,A1 .Location in patent: Paragraph 0390; 0391; 0392; 0393; 0394; 0395

4
3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid [ No CAS ]
[ 90390-33-3 ]
3-amino-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide [ No CAS ]

Reference： [1]Patent: US2013/296274,2013,A1

5
[ 1624255-71-5 ]
[ 90390-33-3 ]
[ 1624256-07-0 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 1704 - 1724

6
[ 67117-22-0 ]
[ 90390-33-3 ]
N-(3-chloro-5-fluorobenzyl)-1-benzyl-3-hydroxypyrrolidine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37 mg	With 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dimethyl sulfoxide; at 0 - 25℃; for 2.0h;	3.2 1 -l3enzyl-3-hydroxypyrrolidine-3-carboxylic acid (100mg) and <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (79 mg) are dissolved in one millilitre of dried DM50 and cooled to 0C. o-(7-Azabenzotrial-l -yl)-N,N,N?,N?-tetramethyluroniumhexafluorophosphate (206 mg) and 4-methylmorpholine (0.124 ml) are then added. The batch is stirred at 25 C. for 2 hours and then immediately purified by chromatography, giving N-(3-chloro-5-fluorobenzyl)-l -benzyl-3-hydroxypyrro- lidine-3-carboxamide (37 mg) as colourless amorphous solid.

Reference： [1]Patent: US2015/31670,2015,A1 .Location in patent: Paragraph 0270; 0274

7
3-hydroxy-2-oxo-1-phenylpiperidine-3-carboxylic acid [ No CAS ]
[ 90390-33-3 ]
N-(3-chloro-5-fluorobenzyl)-3-hydroxy-2-oxo-1-phenylpiperidine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0 - 20℃; for 1.0h;Inert atmosphere;	A solution of 3-hydroxy-2-oxo-1-phenylpiperidine-3-carboxylic acid (80 mg) and <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (65 mg) in dichloromethane (15 ml) is stirred with triethylamine (0.14 ml) and propanephosphoric anhydride (T3P; 0.33 g) firstly at 0 C., then at RT for 1 h under nitrogen. When the reaction is complete, the mixture is diluted with dichloromethane and washed with 10% sodium bicarbonate solution and saturated NaCl solution. Filtration, evaporation and chromatography gives the product as colourless solid with a yield of 12% (15 mg); 10307] LCMS: mass found (M+1,377.0)10308] Method: A-0. 1% ofTFA in H20, B-O. 1% of TFA in ACN: flow-2.0 ml/min.10309] Column: X Bridge C8 (50x4.6 mm.3.5p)+ve mode10310] Rt (mm): 4.03 area % 92.24 (max), 91.79 (220 nm)10311] HPLC:10312] Method: A: 0.1% of TFA in H20, B: 0.1% ofTFA in ACN, flow rate:2.0 ml/min10313] COLUMN: XBridge C8 (50x4.6) mm, 3.5 tm10314] Rt (mm): 4.01 area % 94.30 (max), 94.44 (220 nm);

Reference： [1]Patent: US2015/31670,2015,A1 .Location in patent: Paragraph 0305 - 0314

8
2-oxo-1-phenylazepane-3-carboxylic acid [ No CAS ]
[ 90390-33-3 ]
N-(3-chloro-5-fluorobenzyl)-2-oxo-1-phenylazepane-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0 - 20℃;	Triethylamine (0.74 ml) and propanephosphoric anhydride (T3P; 1.02 g) are added at 0 C. to a solution of 2-oxo-1-phenylazepane-3-carboxylic acid (250 mg) and <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (205 mg) in dichloromethane (15 ml). When the reaction has been brought to completion at RT, the mixture is diluted with further dichloromethane and washed with 10% sodium bicarbonate solution and saturated NaCl solution. The organic phase is treated in the usual manner, and the residue is purified, giving the product as colourless solid in a yield of 87% (350 mg); 10430] LCMS: mass found (M+1,375.2)10431] MethodA: 0.1%ofTFAinH2O, B: 0.1%ofTFAin ACN: flow-2.0 ml/min.10432] Column: X Bridge C8 (50x4.6 mm, 3.5 tm)+ve mode10433] Rt (mm): 4.57 area % 98.66 (max), 97.22 (220 nm) 10434] HPLC:10435] MethodA: 0.1% of TFA in H20, B: 0.1% of TFA inACN, flow rate: 2.0 ml/min10436] Column: XBridge C8 (50x4.6) mm, 3.5 tm10437] Rt (mm): 4.63 area % 97.55 (max), 97.87 (220 nm);10438] ?H NMR (400 MHz, DMSO-d5): oe [ppm]8.37-8.36(m, 1H), 7.40-7.36 (m, 2H), 7.27-7.20 (m, 6H), 4.44-4.38 (m,1H), 4.25-4.20 (m, 1H), 3.92-3.83 (m, 2H), 3.60-3.59 (m,1H), 2.03-2.01 (m, 1H), 1.98-1.95 (m, 1H), 1.78-1.63 (m,4H).

Reference： [1]Patent: US2015/31670,2015,A1 .Location in patent: Paragraph 0428 - 0438

9
[ 1193381-96-2 ]
[ 90390-33-3 ]
1-(1H-benzimidazol-2-yl)-N-(3-chloro-5-fluorobenzyl)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 96.0h;	The compound of intermediate 2 (122 mg, 535 mumomicronIota) was provided in DMF (1.5 mL). N,N-diisopropylethylamine (280 mu, 1.6 mmol), propane phosphonic acid anhydride (T3P, 470 mu, 50% in DMF, 800 mumomicronIota) and <strong>[90390-33-3]1-<strong>[90390-33-3](3-chloro-5-fluorophenyl)methanamine</strong></strong> (128 mg, 802 mumomicronIota) were added, and the mixture was stirred at room temperature for 4 days. After concentration, the remaining material was triturated with ethanol and water and the mixture was stirred for 15 minutes. The precipitate was collected by filtration, and was dried under reduced pressure. 156 mg (76% of theory) of the title compound were obtained. LC-MS (method 2): Rt = 1.12 min; MS (ESIpos): m/z = 370 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 2.323 (0.77), 2.327 (1.12), 2.332 (0.77), 2.523 (2.87), 2.665 (0.83), 2.669 (1.10), 2.674 (0.79), 2.729 (1.58), 2.889 (2.01), 4.481 (9.75), 4.496 (9.57), 7.167 (2.39), 7.174 (3.41), 7.177 (2.74), 7.191 (2.58), 7.195 (3.49), 7.198 (3.56), 7.201 (3.44), 7.205 (1.69), 7.219 (5.21), 7.224 (8.57), 7.233 (8.41), 7.242 (9.14), 7.247 (5.78), 7.260 (2.05), 7.272 (4.61), 7.277 (8.15), 7.280 (5.04), 7.313 (2.86), 7.318 (4.09), 7.324 (2.31), 7.335 (2.91), 7.341 (4.03), 7.346 (2.29), 7.457 (0.65), 7.466 (4.06), 7.470 (3.35), 7.476 (2.58), 7.483 (3.11), 7.489 (3.27), 7.500 (0.48), 7.597 (0.57), 7.607 (3.75), 7.613 (3.15), 7.620 (2.44), 7.626 (2.94), 7.630 (3.32), 7.638 (0.53), 7.823 (0.57), 8.306 (16.00), 8.986 (2.34), 9.001 (4.83), 9.015 (2.25), 9.138 (15.50), 13.287 (5.95).

Reference： [1]Patent: WO2016/202756,2016,A1 .Location in patent: Page/Page column 30

10
[ 36821-26-8 ]
[ 90390-33-3 ]
N-[(3-chloro-5-fluoro-phenyl)methyl]-2-oxo-pyrrolidine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.32%	In 5,5-dimethyl-1,3-cyclohexadiene; at 130℃; for 56.0h;	A solution of compound ethyl 2-oxopyrrolidine-3-carboxylate (180.00 g, 929.61 mmol) and (3-chloro-5-fluorophenyl) methanamine (148.36 g, 929.61 mmol) in xylene (4.00 L) is heated to 130 C for 16 hours. LCMS showed the starting material is still present. The reaction mixture is cooled to 10 C and a solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (3 x500 mL), petroleum ether (2x500 mL), and dried under vacuum to give the desired product (81 g). The filtrates are concentrated under reduced pressure and the residue in xylene (3 L) is heated to 130 C for 40 hours. The reaction mixture is cooled to 10 C and the solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (2x500 mL), petroleum ether (2x500 mL) and dried in vacuum to give the title product (81.38 g) which is combined with the first lot to give a title product (164.38 g, 607.26 mmol, 65.32% yield) as a white solid. ES/MS m/z 270.9 (M+l).
164.38 g	In 5,5-dimethyl-1,3-cyclohexadiene; at 130℃; for 16.0h;	A solution of ethyl 2-oxopyrrolidine-3-carboxylate (180.00 g, 929.61 mmol) and (3-chloro-5-fluoro-phenyl) methanamine (148.36 g, 929.61 mmol) in xylene (4.00 L) is heated to 130 for 16 hours. The reaction mixture is cooled to 10 and a solid precipitates after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (3×500 mL) , petroleum ether (2×500 mL) and dried in vacuum to give the title product (81 g) . The filtrates are concentrated under reduced pressure and the residue in xylene (3 L) is heated to 130 for 40 hours. The reaction mixture is cooled to 10 and solid precipitates after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (2×500 mL) , petroleum ether (2×500 mL) , and dried in vacuum to give the title product (81.38 g) . The combined product (164.38 g, 607.26 mmol, 65.32) is obtained as a white solid. ES/MS m/z 270.9 (M+H) .

Reference： [1]Patent: WO2018/102256,2018,A1 .Location in patent: Page/Page column 11
[2]Patent: WO2017/5069,2017,A1 .Location in patent: Page/Page column 10

11
[ 90390-33-3 ]
(3R)-N-[(3-chloro-5-fluoro-phenyl)methyl]-3-hydroxy-2-oxo-pyrrolidine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

12
[ 90390-33-3 ]
tert-butyl 4-[5-[(3S)-3-[(3-chloro-5-fluorophenyl)methylcarbamoyl]-3-hydroxy-2-oxopyrrolidin-1-yl]-2-pyridyl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

13
[ 90390-33-3 ]
(3S)-N-[(3-chloro-5-fluorophenyl)methyl]-3-hydroxy-2-oxo-1-[6-(piperazin-1-yl)pyridin-3-yl]pyrrolidine-3-carboxamide monohydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

14
[ 90390-33-3 ]
tert-butyl N-[(2R,3S,5R)-5-[4-[5-[(3S)-3-[(3-chloro-5-fluorophenyl)methylcarbamoyl]-3-hydroxy-2-oxopyrrolidin-1-yl]pyrimidin-2-yl]-3,6-dihydro-2H-pyridin-1-yl]-2-(2,5-difluorophenyl)tetrahydropyran-3-yl]carbamate [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

15
[ 90390-33-3 ]
N-[(3-chloro-5-fluoro-phenyl)methyl]-3-hydroxy-2-oxo-pyrrolidine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

16
[ 90390-33-3 ]
(3S)-1-[2-[1-[(3R,5S,6R)-5-amino-6-(2,5-difluorophenyl)tetrahydropyran-3-yl]-3,6-dihydro-2H-pyridin-4-yl]pyrimidin-5-yl]-N-[(3-chloro-5-fluorophenyl)methyl]-3-hydroxy-2-oxopyrrolidine-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/102256,2018,A1

17
[ 90390-33-3 ]
[ 111-64-8 ]
N-(3-chloro-5-fluorobenzyl)octanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 5℃;	159 mg of <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (1 mmol) was weighed into a dry 50 mL eggplant-shaped reaction flask, and 15 mL of dichloromethane was added.The mixture was stirred until the substrate was completely dissolved. After adding 200 muL of triethylamine, a solution of 194 mg of octanoyl chloride (1.2 mmol in a suitable amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.After vacuum distillation under reduced pressure, silica gel column chromatography was used to give N-(3-chloro-5-fluorobenzyl)octanamide.

Reference： [1]Patent: CN108503559,2018,A .Location in patent: Paragraph 0072-0075

18
[ 90390-33-3 ]
[ 4635-59-0 ]
4-chloro-N-(3-chloro-5-fluorobenzyl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 5℃;	159 mg of <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (1 mmol) was weighed into a dry 50 mL eggplant-shaped reaction flask, and 15 mL of dichloromethane was added.Stir until the substrate was completely dissolved. After adding 200 muL of triethylamine, a solution of 168 mg of chlorobutyryl chloride (1.2 mmol in a suitable amount of dry dichloromethane) was slowly added dropwise in an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.The mixture was separated by silica gel column chromatography under reduced pressure to give 4-chloro-N-(3-chloro-5-fluorobenzyl)butanamide.

Reference： [1]Patent: CN108503559,2018,A .Location in patent: Paragraph 0076-0079

19
[ 90390-33-3 ]
(E)-oct-6-enoyl chloride [ No CAS ]
(E)-N-(3-chloro-5-fluorobenzyl)oct-6-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 5℃;	Weigh 159 mg of <strong>[90390-33-3]3-chloro-5-fluorobenzylamine</strong> (1 mmol) in a dry 50 mL eggplant-shaped reaction flask, add 15 mL of dichloromethane, and stir until the substrate is completely dissolved.After adding 200 muL of triethylamine, 192 mg of (E) oct-6-enoyl chloride (1.2 mmol) dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.The mixture was separated by silica gel column chromatography under reduced pressure to give (E)-N-(3-chloro-5-fluorobenzyl)oct-6-enamide.

Reference： [1]Patent: CN108503559,2018,A .Location in patent: Paragraph 0080-0083

20
(R)-3-hydroxy-2-oxo-1-phenyl-pyrrolidine-3-carboxylic acid [ No CAS ]
[ 90390-33-3 ]
(S)-3-hydroxy-2-oxo-1-phenyl-pyrrolidine-3-carboxylic acid 3-chloro-5-fluorobenzyl amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 5025 - 5039

21
[ 1370018-07-7 ]
[ 90390-33-3 ]
3-(3-chloro-5-fluorobenzylcarbamoyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 5025 - 5039

22
[ 30932-84-4 ]
[ 90390-33-3 ]
1-methyl-2-oxo-pyrrolidine-3-carboxylic acid 3-chloro-5-fluorobenzylamide [ No CAS ]