[ CAS No. 119018-29-0 ]

Name: 119018-29-0|4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide|98%
Brand: Ambeed
SKU: A296669
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Quality Control of [ 119018-29-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 119018-29-0 ]

CAS No. :	119018-29-0	MDL No. :	MFCD02955393
Formula :	C₁₆H₂₁N₃O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	351.42 g/mol	Pubchem ID :	11772520
Synonyms :

Calculated chemistry of of [ 119018-29-0 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	93.48
TPSA :	117.95 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.23
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	0.49
Log Po/w (SILICOS-IT) :	0.87
Consensus Log Po/w :	1.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	1.07 mg/ml ; 0.00304 mol/l
Class :	Soluble
Log S (Ali) :	-3.3
Solubility :	0.174 mg/ml ; 0.000496 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.22
Solubility :	0.0213 mg/ml ; 0.0000607 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.92

Safety of [ 119018-29-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 119018-29-0 ]

* 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 [ 119018-29-0 ]
Downstream synthetic route of [ 119018-29-0 ]

[ 119018-29-0 ] Synthesis Path-Upstream 1~10

1
[ 32175-00-1 ]
[ 119018-29-0 ]
[ 93479-97-1 ]

Reference： [1] Patent: CN108383768, 2018, A, . Location in patent: Paragraph 0103-0106

2
[ 119043-16-2 ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
8.47 kg	With ammonium hydroxide In methanol at 20 - 30℃; for 2 h; Industrial scale	38.0 kg of methanol was sequentially added to a 100 L reactor.Industrial ammonia water 5.1Kg; start stirring,Add the above intermediate 2 crude wet product at 20-30 ° C,And the reaction was kept for 2 hours; the sample was controlled by HPLC, and the reaction was completely filtered and washed with water.The obtained white intermediate 3 crude wet product was directly charged into another 200 L reaction kettle.Further, 110.0 kg of methanol was added, and the temperature was raised to 65-75 ° C, and the mixture was stirred for 4 hours.Cool down to 20-25 ° C, filter,Drying white solid intermediate 3 refined product 8.47kg, HPLC purity >99percent,The meta isomer impurity was 0.2

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855
[2] Patent: WO2006/103690, 2006, A1, . Location in patent: Page/Page column 7,14-15
[3] Patent: CN108383768, 2018, A, . Location in patent: Paragraph 0101; 0102

3
[ 35303-76-5 ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 20℃;	3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85percent); mp 183–185 °C.1H NMR (400 MHz, DMSO-d6): δ = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): δ = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140.

Reference： [1] Synlett, 2017, vol. 28, # 18, p. 2495 - 2498

4
[ 247098-17-5 ]
[ 119018-29-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855

5
[ 607-97-6 ]
[ 119018-29-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855

6
[ 766-36-9 ]
[ 119018-29-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855
[2] Synlett, 2017, vol. 28, # 18, p. 2495 - 2498
[3] Patent: CN108383768, 2018, A,

7
[ 247098-18-6 ]
[ 119018-29-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855
[2] Patent: CN107935903, 2018, A,
[3] Patent: CN108383768, 2018, A,

8
[ 61892-80-6 ]
[ 119018-29-0 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855

9
[ 622-24-2 ]
[ 119018-29-0 ]

Reference： [1] Patent: CN107963988, 2018, A,
[2] Patent: CN107935903, 2018, A,

10
[ 1943-82-4 ]
[ 119018-29-0 ]

Reference： [1] Patent: CN108383768, 2018, A,

[ 119018-29-0 ] Synthesis Path-Downstream 1~22

1
[ 599174-27-3 ]
[ 119018-29-0 ]
[ 599174-28-4 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

2
[ 119043-16-2 ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
97.8%	With ammonia; In water; at 80℃; for 1.5h;	120 g of chlorosulfonic acid was added to a three-necked bottle, and the compound m was added in portions. After the addition, the reaction was kept at 80 C for 0.5 hour. The reaction was completely monitored by TLC, and the temperature was lowered to 25 C. The reaction was dropped into ice water and filtered to obtain a solid. Adding solid to a solution of 200 ml of ammonia water and 100 ml of water, heating to 80 C for 1.5 hours, cooling to 30 C, adding hydrochloric acid to the reaction solution, separating the solid, filtering, washing with water, drying at 50 C, The obtained white solid was 25.2 g, and the purity by HPLC was 78.08%, the impurity V 7.24%, the impurity was 16.35%, and the yield was 97.8%.
	With ammonia; at 70℃; for 3 - 4h;	Example 2Preparation of 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl ] benzene sulfonamide (IV)3-Ethyl-4-methyl-2,5-dihydro-lH- pyrrole-2-one (II) (1.0 Kg) and beta-phenylethyl isocyanate (1.488 Kg) were mixed in anhydrous toluene (4.0 L) and refluxed for 4 hrs. The toluene was distilled off and hexane (8.0 L) was added to the reaction mixture at 5O0C. The product precipitated is cooled to 0 to 5 C to obtain the solid compound viz. 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene (2.17 Kg). It was filtered & washed with 2.0 L of hexane.To a cooled (15 to 25 C) solution of chlorosulfonic acid (2.8 L), 4-[2-(3-Ethyl-4- methyl-2-carbonyl pyrrolidine amido) ethyl] benzene (2.0 Kg) was added in small portions over a period of 2 to 3 hrs. Further it was stirred for 30 min at this temperature and then temperature was gradually raised to 30 to 350C. The reaction mass is stirred further for 2 hrs. The reaction mixture was then quenched into ice- water and stirred for 1 hr and filtered to obtain the product 4-[2-(3-Ethyl-4-methyl-2- carbonyl pyrrolidine amido) ethyl] benzene sulfonyl chloride (2.0 kg). To a cooled (15 to 200C) solution of diluted ammonia (1.4 L) 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonyl chloride was added in small portion over 1 to 2 hrs. The reaction mixture was then heated to 7O0C for 2 hrs when ammonolysis is complete. The product converted is then stirred for 1 hr at R.T. and filtered and dried at 90. to 100 C to obtain crude 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (2.2 Kg) having HPLC purity in the range of 82 to 88%. The crude compound 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (2.2 Kg) is then purified from mixture of organic solvents chosen from Methanol, Acetone & toluene.
8.47 kg	With ammonium hydroxide; In methanol; at 20 - 30℃; for 2h;Industrial scale;	38.0 kg of methanol was sequentially added to a 100 L reactor.Industrial ammonia water 5.1Kg; start stirring,Add the above intermediate 2 crude wet product at 20-30 C,And the reaction was kept for 2 hours; the sample was controlled by HPLC, and the reaction was completely filtered and washed with water.The obtained white intermediate 3 crude wet product was directly charged into another 200 L reaction kettle.Further, 110.0 kg of methanol was added, and the temperature was raised to 65-75 C, and the mixture was stirred for 4 hours.Cool down to 20-25 C, filter,Drying white solid intermediate 3 refined product 8.47kg, HPLC purity >99%,The meta isomer impurity was 0.2 <%, and the molar yield was 64% (based on the intermediate 1).

Reference： [1]Patent: CN110092739,2019,A .Location in patent: Paragraph 0022
[2]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855
[3]Patent: WO2006/103690,2006,A1 .Location in patent: Page/Page column 7,14-15
[4]Patent: CN108383768,2018,A .Location in patent: Paragraph 0101; 0102

3
[ 766-36-9 ]
[ 119018-29-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855
[2]Synlett,2017,vol. 28,p. 2495 - 2498
[3]Patent: CN108383768,2018,A

4
[ 61892-80-6 ]
[ 119018-29-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

5
[ 247098-17-5 ]
[ 119018-29-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

6
[ 607-97-6 ]
[ 119018-29-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

7
[ 247098-18-6 ]
[ 119018-29-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855
[2]Patent: CN107935903,2018,A
[3]Patent: CN108383768,2018,A

8
[ 119018-29-0 ]
trans-hydroxyglimepiride [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

9
[ 119018-29-0 ]
cis-hydroxyglimepiride [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4853 - 4855

10
[ 541-41-3 ]
[ 119018-29-0 ]
C₁₉H₂₅N₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; In dichloromethane; at 5 - 30℃;	Examples: Example 1: Preparation of carbamate of Formula IX (R'= ethyl, and Grp1=D) In a reaction vessel 100 gm of 4[2-(3-ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide, 72 gm triethyl amine and 1.6 lit dichloromethane were taken and the mixture cooled to 0 C. 46.15 gm of ethyl chloroformate was diluted separately with 200 ml dichloromethane and added into the reaction vessel drop wise while maintaining the temperature at around 5 C and maintained for 2 hours at 5 C and then at 25 to 30 C till completion of reaction. 2 L water and 0.7 L dichloromethane was added and the pH of the reaction mass were adjusted to 4 by addition of acetic acid. The organic layer was separated and washed with water and concentrated to dryness. The residue was refluxed with 300 ml acetone and cooled to 25 to 30 C, maintained for 1 hour, filtered and washed with 100 ml chilled acetone to get 100 gm carbamate of Formula IX (yield 83percent, purity 99.7percent). Melting Point: 177 to 182 C
83%	With triethylamine; In dichloromethane; at 0 - 30℃; for 2h;	In a reaction vessel 100 g of 4[2-(3-ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide, 72 g triethyl amine, and 1.6 L of dichloromethane were mixed and cooled to 0° C. 46.15 g of ethyl chloroformate was diluted separately with 200 mL of dichloromethane and added into the reaction vessel drop wise while maintaining the temperature at around 5° C. for 2 hours, and then at 25 to 30° C. until completion of the reaction. 2 L of water and 0.7 L of dichloromethane were added; and the pH of the reaction mass was adjusted to 4 by addition of acetic acid. The organic layer was then separated, washed with water, and concentrated to dryness. The residue was refluxed with 300 mL of acetone and cooled to 25 to 30° C., maintained for 1 hour, filtered, and washed with 100 mL of chilled acetone to obtain 100 g carbamate of Formula IX (yield 83percent, purity 99.7percent, and melting point: 177 to 182° C.).

Reference： [1]Patent: EP1700848,2006,A1 .Location in patent: Page/Page column 8
[2]Patent: US2007/255056,2007,A1 .Location in patent: Page/Page column 5-6

11
trans-4-methyl cyclohexyl isocyanate [ No CAS ]
[ 119018-29-0 ]
[ 93479-97-1 ]

Yield	Reaction Conditions	Operation in experiment
~ 50%		4- [2- (3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide(100g) was dissolved in tetrahydrofuran (1800 ml) by stirring and gradually heating to reflux. The reaction mixture was cooled to50-55 C and dryK2CO3 (61 g) was added to it and heated gradually to reflux and maintained for 6 hours. Approximately 300 ml of solvent was distilled of from the reaction mixture during this time.Trans-4-methylyclohexyl isocyanate(221g) in toluene (24.46percent w/w) was added to the reaction mixture at reflux temperature in 5-10 minutes. The reaction mixture was refluxed for 6 hours and then cooled to40-45 C and filtered at this temperature. The product was washed with tetrahydrofuran (300 ml) and suck dried for 30 minutes. Then it was taken into DM water(2000ml) and stirred for 15 min at25-30 C, the pH was adjusted to 6-6.5 withHC1 solution (130 ml, 1: 1) and stirred for 30 minutes at20-25 C. Then pH was brought to 8- 8.5 by drop wise addition of 5percent aq KOH solution (about 20 ml) and stirred for 30 minutes at25-30 C. The product was filtered and washed with water (400 ml), followed by methanol (20 ml), suck dried and slurried in water (2000 ml) for 1 hour at45-50 C and filtered. The wet cake was slurried in toluene (1000 ml) for 1 hour at 80-85 C, cooled and filtered, washed with toluene, followed by methanol to obtain glimepiride, wet weight: 200g (moisturecontent-50percent).

Reference： [1]Patent: WO2005/49532,2005,A2 .Location in patent: Page/Page column 10

12
[ 32175-00-1 ]
[ 119018-29-0 ]
[ 93479-97-1 ]

Yield	Reaction Conditions	Operation in experiment
94.5%	In tert-butyl methyl ether; cyclohexanone; at 30℃; for 10h;	2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonamide (F) prepared in Example 5 (2.6 g, 1.37 mol )After being mixed with trans-p-methylcyclohexyl isocyanate (G) (2.1 g, 1.64 mol), it was dissolved in a mixture of cyclohexanone (45 ml) and methyl tert-butyl ether (30 ml), and heated to 30°C in a water bath. ,After stirring for 10 hours, the heating was stopped, and the mixture was naturally stirred and cooled to 10° C., poured into water, extracted with dichloromethane (90 ml), concentrated, dissolved in ethanol, and crystallized at 3° C.Dry to give 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-3 -(trans-4-methylcyclohexyl)-urea (H) (3.74 g), yield 94.5percent, purity 99.82percent.
86.3%		Example 4Preparation of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans;-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo- 1 H-pyrrole- 1 - carboxamide (I).In a reaction vessel containing (24.2 L) Acetone, 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (1.0 Kg) and potassium carbonate (0.46 Kg) was added and refluxed at about 55 to 60 C for 1 hr. trans-4-Methyl- cyclohexyl isocyanate was obtained by method known in art from trans-4-methyl- cyclohexylamine. A solution of trans-4-methyl-cyclohexyl isocyanate (0.515 Kg) in toluene (5 L) was prepared and added to the above reaction mixture. This reaction mixture is refluxed for 12 lirs, then cooled. To this cooled reaction mass charge 27 L of water. The reaction mass was filtered and the pH was adjusted to 5.5 to 6.0 by adding acetic acid at about 20 to 250C. The solid obtained was filtered and washed with water. The 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(/7-?ro-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-lH-pyrrole-l- carboxamide (I) obtained is then dried at 90 to 1000C till constant weight. Yield of the product is 86.3percent. Example 5Purification of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(tr?ro-4-methyl cyclohexyl)amino] carbonyl] amino] sulfonyljphenyl] ethyl] -2-oxo- 1 H-pyrrole- 1 - carboxamide (I)In a reaction vessel containing 6.0 L methanol and 1.0 Kg crude Glimepiride, dry ammonia gas was purged at 20 to 25 C till all Glimepiride dissolves and a clear solution is obtained. This homogeneous mass was then charcoalised, filtered and finally neutralized with Glacial acetic acid to pH 5.5 to 6.0, till the entire product precipitates out. The pure Glimepiride was then filtered and dried at 65C to 700C till constant weight. Yield obtained was ~ 90percent.

Reference： [1]Patent: CN107935903,2018,A .Location in patent: Paragraph 0020; 0021
[2]Patent: WO2006/103690,2006,A1 .Location in patent: Page/Page column 7,16

13
[ 210827-31-9 ]
[ 119018-29-0 ]
3-ethyl-N-(4-(N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)sulfamoyl)phenethyl)-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide [ No CAS ]

Reference： [1]ChemMedChem,2017,vol. 12,p. 1449 - 1457

14
phenyl 3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate [ No CAS ]
[ 35303-76-5 ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran; at 20℃;	3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85%); mp 183-185 C.1H NMR (400 MHz, DMSO-d6): delta = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): delta = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140.
85.5%	In isopropyl alcohol; for 6h;Reflux;	The compound Kappa 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g and isopropanol 50g were heated under reflux for 6 h (4-(2-aminoethyl)benzenesulfonamide remaining 0.79%), cooled to After drying at 25 C, filtration and 50 C, 6.12 g of compound I was obtained. The purity of the solution was 98.66% by HPLC, the impurity was 0.60%, and the impurities V and VI were not detected. The yield was 85.5%.

Reference： [1]Synlett,2017,vol. 28,p. 2495 - 2498
[2]Patent: CN110092739,2019,A .Location in patent: Paragraph 0023; 0024; 0025; 0028

15
phenyl ((1r,4r)-4-methylcyclohexyl)carbamate [ No CAS ]
[ 119018-29-0 ]
[ 93479-97-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 5h;Reflux;	Carboxamide 2 (1.054 g, 3 mmol) and carbamate 3 (0.770 g, 3.3mmol) were dissolved in MeCN (40 mL), and DBU (0.685 g, 4 5mmole) was added. The mixture was then refluxed for 5 h until the reaction was complete (TLC). The solvent was evaporatedunder reduced pressure, the residue was dissolved in EtOAc(100 mL), and the solution was extracted with 0.1 N aq HCl (2 ×50 mL). The organic layer was washed with brine (2 × 50 mL),dried (Na2SO4), filtered, and concentrated again under reducedpressure. The crude product was purified by crystallization(MeOH) to give a white solid; yield: 1.255 g (85percent); mp 202?204 °C.1H NMR (400 MHz, DMSO-d6): delta = 8.38 (t, J = 5.6 Hz, 1 H), 7.81(d, J = 8.2 Hz, 2 H), 7.46 (d, J = 8.2 Hz, 2 H), 6.28 (d, J = 7.6 Hz, 1H), 4.16 (s, 2 H), 3.50 (q, J = 6.4 Hz, 2 H), 3.21?3.15 (m, 1 H), 2.90(t, J = 7.1 Hz, 2 H), 2.18 (q, J = 7.5 Hz, 2 H), 2.01 (s, 3 H), 1.68 (d,J = 12.8 Hz, 2 H), 1.59 (d, J = 12.8 Hz, 2 H), 1.23?0.79 (m, 11 H).13C NMR (100 MHz, DMSO-d6): delta = 171.7, 151.9, 151.5, 150.4,144.8, 138.1, 131.8, 129.0, 127.2, 51.8, 48.4, 39.9, 35.1, 33.2,32.2, 31.1, 21.9, 15.9, 12.7, 12.6. HRMS (ESI): m/z [M + Na]+ calcdfor C24H34N4NaO5S:, 513.2148; found: 513.2133.

Reference： [1]Synlett,2017,vol. 28,p. 2495 - 2498

16
trans-4-methylcyclohexylamine [ No CAS ]
[ 530-62-1 ]
[ 119018-29-0 ]
glimepiride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.1%		Under nitrogen protection,In the reactor,N-4- [2- (3-ethyl-4-methyl-2-oxo-3-pyrroline- 1 -carboxamido) ethyl] -benzenesulfonamide (33.6 g, 0.1 mol)Hexamethylphosphoric triamide (200 mL),1,8-diazabicyclo [5,4,0] undecene-7 (15.2 g, 0.1 mol),Then N, N'-carbonyldiimidazole (32.4 g, 0.2 mol),After heating to 80 ° C for 3 hours, hexamethylphosphoric triamide (20 mL) of trans 4-methylcyclohexylamine (11.3 g, 0.1 mol)The reaction was heated overnight,TLC detection and tracking reaction,After the disappearance of raw materials completely,Stop stirring,cool down,Suction filtration,Washed,Dry glimepiride 41.6gWhite solid.Melting at 207-208 ° C,The yield was 85.1percent

Reference： [1]Patent: CN107400077,2017,A .Location in patent: Paragraph 0018; 0020; 0021; 0022

17
3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamide [ No CAS ]
[ 119018-29-0 ]

Reference： [1]Patent: CN107963988,2018,A
[2]Patent: CN107935903,2018,A

18
[ 622-24-2 ]
[ 119018-29-0 ]

Reference： [1]Patent: CN107963988,2018,A
[2]Patent: CN107935903,2018,A

19
4-{2-[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl)amino]ethyl}benzene-1-sulfonic acid [ No CAS ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
90.28%	With ammonia; In 1,4-dioxane; at 35℃;	2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid prepared in Example 3 (E)(3.8 g, 1.64 mol) was dissolved in a flask containing dioxane (40 ml) and ammonia gas was introduced at 35°C.After the reaction was completed, dilute with dichloromethane (60 ml).The organic phase was concentrated, washed with water, recrystallized from ethanol, and dried to give 3-ethyl-4-methyl-2-oxo-N-[2-(4-sulfamoylphenyl)ethyl]-2,5-dihydro-1H-pyrrole-1-carboxamide (F ) (3.11g),The yield was 90.28percent and the purity was 99.69percent.
90.28%	With ammonia; In 1,4-dioxane; at 35℃;	2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid (E) prepared in Example 3 (3.8 g, 1.64 mol )Dissolve in a flask containing dioxane (40ml) and introduce ammonia gas at 35°C.2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonamide (F) (3.11 g) was prepared,The yield was 90.28percent and the purity was 99.69percent.

Reference： [1]Patent: CN107963988,2018,A .Location in patent: Paragraph 0005; 0017-0018
[2]Patent: CN107935903,2018,A .Location in patent: Paragraph 0018; 0019

20
[ 32175-00-1 ]
[ 119018-29-0 ]
[ 93479-97-1 ]

Yield	Reaction Conditions	Operation in experiment
		Add 67 kg of acetonitrile to the 200 L reactor.Intermediate 3 refined product 8.47kg, potassium carbonate 4.00kg,Turn on the agitation and warm to 50-60 ° C.6.01 kg of trans-4-methylcyclohexyl isocyanate was added, and the reaction was continued for 6 hours.Sampling HPLC control, the reaction is complete, filtered, washed,The obtained glimepiride metal salt crude wet product is put into the next step to remove the insoluble matter. Step 5: remove insolubles, acidify, and refine Adding the above-mentioned glimepiride metal salt crude wet product and 10 times by weight of purified water to a 500 L reaction kettle,Stir at 70-75 ° C for 4 hours, heat filter, filter residue to waste treatment station,The filtrate enters the clean room 500L reactor and is cooled to 20-25 °C.Add 15percent hydrochloric acid to adjust pH=1-2, filter, wash,The obtained glimepiride crude wet product is reflowed by refluxing with 5 times by weight of acetone of glimepiride crude wet product.It is then cooled to room temperature, filtered and dried to obtain a finished glimepiride.HPLC purity >99.5percent,The molar yield was 80percent (based on the intermediate 3 refined product).

Reference： [1]Patent: CN108383768,2018,A .Location in patent: Paragraph 0103-0106

21
[ 1943-82-4 ]
[ 119018-29-0 ]

Reference： [1]Patent: CN108383768,2018,A

22
C₂₄H₃₀N₄O₆S [ No CAS ]
[ 35303-76-5 ]
[ 119018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
93.6%	With propionic acid; In isopropyl alcohol; for 7.5h;Reflux;	10.0 g of the compound, 8.16 g of 4-(2-aminoethyl)benzenesulfonamide, 3.02 g of propionic acid and 50 g of isopropanol were heated under reflux for 7.5 h, cooled at 25 C, filtered and dried at 50 C to give the compound 113.52 g. , the yield was 94.4%, the purity of the HPLC method was 99.63%, the impurity was 0.06%, and the impurities V and VI were not detected.

Reference： [1]Patent: CN110092739,2019,A .Location in patent: Paragraph 0028; 0029; 0030; 0031

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[ CAS No. 119018-29-0 ]

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[ 119018-29-0 ] Synthesis Path-Upstream 1~10

[ 119018-29-0 ] Synthesis Path-Downstream 1~22

Related Functional Groups of [ 119018-29-0 ]

Sulfamides

Amines

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Aryls

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Aliphatic Heterocycles

Pyrrolines

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