[ CAS No. 147962-41-2 ] {[proInfo.proName]}

Name: 147962-41-2|N-Propylsulfamide|97%
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Product Details of [ 147962-41-2 ]

CAS No. :	147962-41-2	MDL No. :	MFCD12755184
Formula :	C₃H₁₀N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FEYGBGVBTKYFOF-UHFFFAOYSA-N
M.W :	138.19	Pubchem ID :	13949558
Synonyms :

Safety of [ 147962-41-2 ]

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 [ 147962-41-2 ]

* 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.

Upstream synthesis route of [ 147962-41-2 ]
Downstream synthetic route of [ 147962-41-2 ]

[ 147962-41-2 ] Synthesis Path-Upstream 1~4

1
[ 107-10-8 ]
[ 1189-71-5 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With triethylamine; benzyl alcohol In dichloromethane at -50 - 20℃; for 2 h; Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; for 6 h;	A.i. Propane-1-sulfamide; Chlorosulfonyl isocyanate (12.3 mL; 0.14 mol; 1.0 eq.) was slowly added to a cold (- 35°C) solution of benzyl alcohol (14.7 mL; 0.14 mol; 1.0 eq.) in DCM (130 mL) over 30 min. A solution of n-propylamine (14 mL, 0.17 mol; 1.2 eq.) and triethylamine (29.5 mL; 0.21 mol; 1.5 eq.) in DCM (35 mL) was slowly added dropwise at -50°C. The mixture was warmed to 20°C for 2 h. It was washed with water, followed by aq. 33percent HCl and water. The mixture was warmed to 30°C and the layers were separated. The org. phase was washed with a mixture of Et₃N (20 mL; 0.14 mol; 1 eq.) and water (50 mL) so that pH > 5. THF (85 mL) was added followed by 10percent> Pd/C (1 g). The reaction mixture was hydrogenated at 25°C for 6 h under 6 bars of hydrogen. It was filtered over Celite. The volatiles were removed. DMSO (120 mL) was added. The solution of propane-1-sulfamide (100percent theoretical yield) thus obtained in DMSO was used as such in the next step

Reference： [1] Patent: WO2015/4265, 2015, A1, . Location in patent: Page/Page column 25; 26

2
[ 1393813-40-5 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	Reflux	General procedure: The deprotection reaction of sulfonamide (1a–e) (1g) was carried out in distilled water (30 mL); the reaction mixture was refluxed for 15–30 min, then it was extracted with ethyl acetate (3 × 30 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give sulfonamides (2a–e) in good yields.

Reference： [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2014, vol. 189, # 5, p. 587 - 595
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7849 - 7861
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 3, p. 269 - 276
[4] Molecular Diversity, 2016, vol. 20, # 2, p. 399 - 405
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 10, p. 1344 - 1350

3
[ 107-10-8 ]
[ 147962-41-2 ]

Reference： [1] Patent: WO2014/155304, 2014, A1, . Location in patent: Page/Page column 24

4
[ 10305-42-7 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
122.8 g	With ammonia In dichloromethane at 20℃; for 1 h; Inert atmosphere	Under the protection of nitrogen, 155 g of the compound of formula III was added to the clean four-necked reaction flask, 300 ml of dichloromethane was added,Stir,Temperature control at about 20 ,Slowly into the ammonia for about 1 hour,The reaction solution was concentrated under reduced pressure to obtain 132.5 g of the crude compound of formula V.The resulting crude compound was distilled to give 122.8 g of the compound of formula V as a colorless and transparent liquid. The total yield of the two steps was 88.8percent (based on the compound of formula I). GC purity was 99.5percent.

Reference： [1] Patent: CN107141238, 2017, A, . Location in patent: Paragraph 0029-0032; 0036-0039; 0043-0046; 0050-0053

[ 147962-41-2 ] Synthesis Path-Downstream 1~28

1
[ 147962-41-2 ]
[ 3923-79-3 ]
[ 24039-08-5 ]
[ 1054462-99-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 981 - 988

2
[ 147962-41-2 ]
[ 53629-29-1 ]
[ 71886-28-7 ]
C₁₀H₂₀N₄O₃S [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 981 - 988

4
[ 147962-41-2 ]
[ 112-90-3 ]
N-oleyl-N'-propylsulfamide [ No CAS ]
N,N'-dioleylsulfamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4889 - 4895

5
[ 147962-41-2 ]
[ 3923-79-3 ]
[ 1054462-99-5 ]
[ 1202684-08-9 ]

Reference： [1]Russian Chemical Bulletin,2008,vol. 57,p. 1744 - 1753

6
[ 147962-41-2 ]
[ 3923-79-3 ]
[ 1202684-08-9 ]

Reference： [1]Russian Chemical Bulletin,2008,vol. 57,p. 1744 - 1753

7
[ 147962-41-2 ]
[ 53629-29-1 ]
[ 1202684-09-0 ]
[ 1054463-01-2 ]

Reference： [1]Russian Chemical Bulletin,2008,vol. 57,p. 1744 - 1753

8
[ 1393813-40-5 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	In water;Reflux;	General procedure: The deprotection reaction of sulfonamide (1a-e) (1g) was carried out in distilled water (30 mL); the reaction mixture was refluxed for 15-30 min, then it was extracted with ethyl acetate (3 × 30 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give sulfonamides (2a-e) in good yields.
	at 110℃; for 0.25h;	General procedure: The sulfonamides was prepared from carboxylsulfamides (1 mmol) in water and stirred at reflux temperature. After 15 min the resulting reaction solution was extracted by ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure
	In water; at 110℃; for 0.25h;	General procedure: The sulfonamides was prepared from carboxylsulfamides (1 mmol) inwater and stirred at reflux temperature. After 15 min the resulting reactionsolution was extracted by ethyl acetate. The organic layer is dried overmagnesium sulfate and concentrated under reduced pressure. Thespectral data of compounds (1a-i) and (2a-i) is shown in the SupplementalMaterials of reference [54].

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,p. 587 - 595
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7849 - 7861
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 269 - 276
[4]Molecular Diversity,2016,vol. 20,p. 399 - 405
[5]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 1344 - 1350

9
[ 147962-41-2 ]
potassium (N-propylsulfamoyl)amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7849 - 7861

10
[ 147962-41-2 ]
[ 150727-28-9 ]
C₁₄H₁₇ClN₄O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7849 - 7861

11
[ 150727-65-4 ]
[ 147962-41-2 ]
C₁₄H₁₆Cl₂N₄O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7849 - 7861

12
[ 147962-41-2 ]
[ 3974-18-3 ]
C₁₃H₁₄Cl₂N₄O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7849 - 7861

13
[ 147962-41-2 ]
[ 108-24-7 ]
[ 1399296-10-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With H6P2W18O62 heteropolyacid; In acetonitrile; at 20℃; for 0.366667h;Inert atmosphere;	General procedure: Under nitrogen atmosphere , amixture ofsulfamide (1mmol), acetic anhydrid e (1.5mmol)and H6P2W18O62 catalyst (1 mmol%) in acetonitri le (2mL),was stirred atroom temperature . Reaction was monitored by TLC.After completion ofthe reaction,the sol- vent was evaporated, diluted with 10mLofwater tosolubilise the catalyst, and extracted with EtOAc (3 15 mL),the combined organic layers were dried over anhydrous Na2SO4, then the solvent was evaporated in vacuum,and the crude compound was purified by flashchromatograp hy (Mercksilica gel 60H,CH2Cl2/MeOH, 9:1) to afford the correspondi ng acyl-sulfam ide.Entry (b), N-(N-propylsu lfamoyl) acetamide.
90%	In water; at 20℃; for 0.233333h;Green chemistry;	In a 50mL round-bottomed flask, a mixtureof amine or amino alcohol (1 mmol) and aceticanhydride (1.2 mmol) was stirred at roomtemperature for the appropriate time. Aftercompletion of the reaction, as monitored by TLC,the reaction mixture was dissolved in ether (5 mL)and was allowed to stand at room temperature for1 hour. During this time, crystal of product formed,which were collected by filtration.In the case of solid substrates(sulfonamides), the same protocol was used.However, the use of water was required for thesolubility of the mixture. The N-acylatedsulfonamides were collected by crystallization fromdiethyl ether.
90%	In neat (no solvent); at 20℃; for 0.25h;Sonication; Green chemistry;	General procedure: In a glass tube was placed a mixture of amine or sulfonamide derivatives (1 equiv) and acetic anhydride (1equiv) at room temperature. The mixture was immersed in the water of the sonicator bath for appropriate time at room temperature. Reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with the water, and extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and the resulting residue was purifed by silica gel chromatography using dichloromethane-petroleum ether (9:1), to give the N-acylamines or N-acylsulfonamides in good yieds.

Reference： [1]Journal of Molecular Structure,2013,vol. 1041,p. 6 - 15
[2]Oriental Journal of Chemistry,2015,vol. 31,p. 913 - 919
[3]Oriental Journal of Chemistry,2017,vol. 33,p. 1454 - 1460

14
[ 97-64-3 ]
[ 147962-41-2 ]
[ 1612186-13-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tin(IV) chloride; In acetonitrile; at 82℃; for 12h;	General procedure: The N-acylation reaction of sulfonamide (2a-e) (2 mmol) with ethyl lactate (0.47 g, 0.46 mL, 4 mmol) was carried out in acetonitrile or toluene (4.5 mL) in the presence of SnCl4 (0.78 g, 0.35 mL, 1.5 equiv., 3 mmol) for 12 h. The reaction mixture was evaporated and diluted with methylene chloride (30 mL) and then washed with water. The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by silica gel chromatography diluted with CH2Cl2 to give N-acysulfonamides(3a-e).

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,p. 587 - 595

15
[ 146533-41-7 ]
[ 147962-41-2 ]
[ 1393813-42-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		A.ii. N-(5-(4-bromophenyl)-6-chloropyrimidin-4-yl)propane-1-sulfamide:tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 mi <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portionwise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HC1. The suspension was cooled to 0C and stirred for 30 mm. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to S -(4-bromophenyl)-4,6-dichloropyrimidine).
89%		A.ii. N- (5 -(4-bromopheny I) -6-chloropyrimidin-4-yl)propane- 1-sulfamide; tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 min. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portion wise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HCl. The suspension was cooled to 0C and stirred for 30 min. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong>).
	With lithium amide; In dimethyl sulfoxide; at 15 - 25℃; for 2h;Inert atmosphere;	To a solution of V-propylsulfamide (25.0 gm, 0.180 mol) in dimethylsulfoxide (250.0 ml) was added Lithium amide (7.6 gm, 0.33 mol) under nitrogen atmosphere at 15-25 C, followed by addition of 5-(4-bromophenyl)-4,6- dichloropyrimidine (50.0 gm, 0.164 mol). The reaction mass was stirred for 2 hr. at room temperature and the progress of reaction was monitored by HPLC. After reaction completion this reaction mass was drop wise added to the solution containing Lithium amide (7.6 gm, 0.33 mol) and ethylene glycol (250.0 ml) at 15-25 C under nitrogen atmosphere. After the addition reaction mixture was heated to 105 - 110C, maintained for 18-24 hours and the reaction progress was monitored by HPLC. After completion of reaction, resulting mass was cooled to 25-30 C and 5% w/v citric acid solution (1000.0 ml) was added to the reaction mass. The product was extracted twice with ethyl acetate (1000.0 ml x 2), further organic layer was washed twice with 10% w/v brine solution (500.0 ml x 2). Organic layer was concentrated at 55-60C under reduced pressure to produce A/-5-(4- bromophenyl)-6-(-2-hydroxyethoxy)-4-pyrimidinyl-//-propylsulfamide as a residue. The obtained residue was dissolved in methanol 65-70 C and maintained for 30 min. The resulting solution was gradually cooled to room temperature then cooled to 0-5C and maintained reaction mass at 0-5C for 60-90 min. Obtained solid was filtered, washed with methanol (50.0 ml), suck dried and dried at 55-60C to afford white solid of N-5-(4-bromophenyl)-6-(- 2hydroxyethoxy)-4-pyrimidinyl- N'-propylsulfamide. [Yield = 50.0 gm (70.48 %); Purity (HPLC) = 98.50 %]. (M + H)7z= 433.0. 1H NMR (CDCl3): delta 8.46-8.45 (s, 1 H), 7.65-7.62 (m, 2H), 7.25-7.17 (m, 2H), 6.91 (s, br, 1 H), 5.62-5.69 (t, 1 H), 4.48-4.46 (m, 2H), 3.84- 3.81 (m, 2H), 2.97-2.92 (q, 2H), 2.97-2.92 (t, 1 H), 1.16-1.52 (h, 2H), 0.94- 0.91 (t, 3H). 3C NMR (CDC ): delta 11.31 , 22.07, 44.74, 59.20, 68.32, 104.94, 121.42, 129.84, 131.55, 132.79, 155.91 , 156.38, 166.26.

		Potassium tert-butoxide(90 gm, 0.802 mol) was added in to a reaction flask containing a solution of N-Propyl-sulfamide (N-Propyl-sulfamide (82 gm, 0.593 mol) in DMSO (250 ml)) and stirred the reaction mass at room temperature for 30 min to obtain potassium salt of N- propyl sulfamide. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (100 gm, 0.329 mol) was added in to the reaction mass and stirred the contents for 5-6 hrs at 25-30C. DM water (500 ml) was added to the reaction mass a stirred solution. Further 10% citric acid solution (500 ml) was added slowly for an about 1 -2 hrs to obtain solid. The precipitated solid was filtered and washed with DM water (120 ml) and suck dried the material for 30 min. The product was dried under vacuum at 50-55 C for 10-12 hrs to obtain title product. Yield: 137 gm; Purity (By HPLC): 92.0%
	With lithium amide; In dimethyl sulfoxide; at 20 - 25℃; for 2h;	To a stirred solution of 2.0 kg 5-(4-Bromophenyl)-4,6-dichloropyrimidine (2, 6.57 mol) in 20 dm3 DMSO,0.303 kg lithium amide (13.15 mol) and 1.0 kg N-propylsulfamide(3, 7.23 mol) were added at 20-25 C. The reaction mass was stirred at 20-25 C for 2-6 h (completionof the reaction was monitored by HPLC).

Reference： [1]Patent: WO2014/155304,2014,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2015/4265,2015,A1 .Location in patent: Page/Page column 26
[3]Patent: WO2016/203489,2016,A1 .Location in patent: Page/Page column 22; 23
[4]Patent: WO2017/191565,2017,A1 .Location in patent: Page/Page column 12; 13
[5]Monatshefte fur Chemie,2018,vol. 149,p. 653 - 661

16
[ 107-10-8 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
		A.i. Propane-1-sulfamide.Chlorosulfonyl isocyanate (12.3 mL; 0.14 mol; 1.0 eq.) was slowly added to a cold (- 35C) solution of benzyl alcohol (14.7 mL; 0.14 mol; 1.0 eq.) in DCM (130 mL) over 30 mm. A solution of n-propylamine (14 mL, 0.17 mol; 1.2 eq.) and triethylamine (29.5 mL; 0.21 mol; 1.5 eq.) in DCM (35 mL) was slowly added dropwise at -50C. The mixture was warmed to 20C for 2 h. It was washed with water, followed by aq. 33% HC1 and water. The mixture was warmed to 30C and the layers were separated. The org. phase was washed with a mixture of Et3N (20 mL; 0.14 mol; 1 eq.) and water (50 mL) so that pH> 5. THF (85 mL) was added followed by 10% Pd/C (1 g). The reaction mixture was hydrogenated at 25C for 6 h under 6 bars of hydrogen. It was filtered over Celite. The volatiles were removed. DMSO (120 mL) was added. The solution of propane-1-sulfamide (100% theoretical yield) thus obtained in DMSO was used as such in the next step.

Reference： [1]Patent: WO2014/155304,2014,A1 .Location in patent: Page/Page column 24

17
[ 107-10-8 ]
[ 1189-71-5 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		A.i. Propane-1-sulfamide; Chlorosulfonyl isocyanate (12.3 mL; 0.14 mol; 1.0 eq.) was slowly added to a cold (- 35C) solution of benzyl alcohol (14.7 mL; 0.14 mol; 1.0 eq.) in DCM (130 mL) over 30 min. A solution of n-propylamine (14 mL, 0.17 mol; 1.2 eq.) and triethylamine (29.5 mL; 0.21 mol; 1.5 eq.) in DCM (35 mL) was slowly added dropwise at -50C. The mixture was warmed to 20C for 2 h. It was washed with water, followed by aq. 33% HCl and water. The mixture was warmed to 30C and the layers were separated. The org. phase was washed with a mixture of Et3N (20 mL; 0.14 mol; 1 eq.) and water (50 mL) so that pH > 5. THF (85 mL) was added followed by 10%> Pd/C (1 g). The reaction mixture was hydrogenated at 25C for 6 h under 6 bars of hydrogen. It was filtered over Celite. The volatiles were removed. DMSO (120 mL) was added. The solution of propane-1-sulfamide (100% theoretical yield) thus obtained in DMSO was used as such in the next step

Reference： [1]Patent: WO2015/4265,2015,A1 .Location in patent: Page/Page column 25; 26

18
[ 108-30-5 ]
[ 147962-41-2 ]
N-(propyl)-2,5-dioxopyrrolidine-1-sulfonamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 269 - 276

19
[ 147962-41-2 ]
[ 100-52-7 ]
[ 122-52-1 ]
C₁₄H₂₅N₂O₅PS [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 39324 - 39329

20
[ 147962-41-2 ]
5-(4-bromophenyl)-4-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)-6-chloropyrimidine [ No CAS ]
macitentan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrabutyl ammonium fluoride; potassium carbonate; In dimethyl sulfoxide; at 100℃; for 1h;	The compound of Example 1 (10 g; 20.6 mmol), propylsulfamide (3.1 g; 22.6 mmol; 1.1 eq.; prepared as described in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861), TBAF.3H20 (19.5 g; 61.7 mmol; 3 eq.) and potassium carbonate (8.5 g; 61.7 mmol; 3 eq.) were suspended in DMSO (100 mL). The mixture was heated to 100C for 1 h and then cooled to 20-25C. Water (100 mL) and DCM (100 mL) were added. The org. layer was washed 3 times with water (100 mL each time), 20% aq. citric acid (100 mL) and water (100 mL) before being concentrated under reduced pressure to dryness. The residue was suspended in EA (15 mL) and heated to reflux. Hept (30 mL) was added. The mixture was allowed to cool to 20-25C on its own. The precipitate was filtered off and rinsed with Hept (10 mL). The beige solid thus collected (11.0 g) was recrystallized from EA (30 mL) and Hept (25 mL) to afford the title compound as a white solid (6.4 g; 53% yield). (0323) The product had MS and NMR data equivalent to those reported in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861. LC-MS (method 1): tR = 1.89 min; 100% a/a.

Reference： [1]Patent: WO2015/121397,2015,A1 .Location in patent: Page/Page column 45; 46

21
[ 147962-41-2 ]
5-(4-bromophenyl)-4-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)-6-fluoropyrimidine [ No CAS ]
macitentan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; cesium fluoride; In dimethyl sulfoxide; at 70 - 75℃; for 15h;	The compound of Example 2 (2 g; 4.25 mmol), propylsulfamide (735 mg; 5.32 mmol; 1.2 eq.; prepared as described in Bolli et al, J. Med. Chem. (2012), 55, 7849-7861), cesium fluoride (2.0 g; 12.8 mmol; 3 eq.) and potassium carbonate (1.7 g; 12.8 mmol; 3 eq.) were suspended in DMSO (20 mL) at 20-25C. The mixture was heated to 70-75C for 15 h. Water (20 mL) and DCM (20 mL) were added. The layers were separated and the org. phase was washed with 30% aq. citric acid (20 mL) before being concentrated to dryness. The residue was recrystallized from toluene to yield the title compound as a white powder (600 mg; 24% yield). (0325) The product had MS and NMR data equivalent to those reported in Bolli et al, J. Med. (0326) Chem. (2012), 55, 7849-7861. (0327) LC-MS (method 1): tR = 1.83 min; 96.7% a/a

Reference： [1]Patent: WO2015/121397,2015,A1 .Location in patent: Page/Page column 46

22
[ 5467-15-2 ]
[ 147962-41-2 ]
N-chloroethyl,N'-(1-propyl)sulfamoylimidazolidine-2-one [ No CAS ]

Reference： [1]Molecular Diversity,2016,vol. 20,p. 399 - 405

23
[ 108-31-6 ]
[ 147962-41-2 ]
N-(propyl)-2,5-dioxopyrrole-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With Dawson acid; In acetonitrile; for 1h;Inert atmosphere; Reflux; Green chemistry;	General procedure: Under nitrogen atmosphere, a mixture of sulfonamide 2a-h (1 mmol), maleic anhydride derivatives (2 mmol), and H6P2W18O62 catalyst (2 mmol%) in acetonitrile (2 mL), was stirred at reflux. Reaction was monitored by TLC. After achieving the reaction, dichloromethane (2 ×10 mL) was added and the catalyst was filtered; water (10 mL) was then added.The organic layers were combined and dried over anhydrous sodium sulfate and removed under reduced pressure. The residue obtained was purified by flash chromatography (Merck silica gel 60H, CH2Cl2/MeOH, 9:1) to afford the corresponding sulfonyl maleimide derivatives.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 1344 - 1350

24
[ 1122-17-4 ]
[ 147962-41-2 ]
N-(propyl)-3,4-dichloro-2,5-dioxopyrrole-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With Dawson acid; In acetonitrile; for 1h;Inert atmosphere; Reflux; Green chemistry;	General procedure: Under nitrogen atmosphere, a mixture of sulfonamide 2a-h (1 mmol), maleic anhydride derivatives (2 mmol), and H6P2W18O62 catalyst (2 mmol%) in acetonitrile (2 mL), was stirred at reflux. Reaction was monitored by TLC. After achieving the reaction, dichloromethane (2 ×10 mL) was added and the catalyst was filtered; water (10 mL) was then added. The organic layers were combined and dried over anhydrous sodium sulfate and removed under reduced pressure. The residue obtained was purified by flash chromatography (Merck silica gel 60H, CH2Cl2/MeOH, 9:1) to afford the corresponding sulfonyl maleimide derivatives.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 1344 - 1350

25
[ 146533-41-7 ]
[ 147962-41-2 ]
[ 107-21-1 ]
C₂₈H₃₂Br₂N₈O₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1, 8 ml of N, N-dimethylformamide, 100 g (724 mmol) of N-propylsulfamide, 26 g (1083 mmol) of sodium hydride were added to the 1 L three-necked reaction flask, and the mixture was stirred at 10 to 15 C for 30 min, (724 mmol) of 4-bromophenyl-4,6-dichloropyrimidine was stirred at 20-25 C for 8 h and then stirred at 35-40 C for 1 h, cooled to 10-15 C,22.3 g (35.9 mmol) of ethylene glycol was added,And p-toluenesulfonyl chloride (137 g, 71.9 mmol) were added and the temperature was raised to 85-95 C. The reaction was continued for 9 h, cooled to 0-10 C. The solution was crystallized by adding 10 wt% citric acid aqueous solution. The filter cake was washed with purified water neutral,The solid was collected and dried at 40-50 C under vacuum (vacuum ? 0.08 MPa) for 8 h to give 212.5 g of crude impurities and 73.9% yield. 2, to 212.5g impurity crude addition of ethyl acetate 700ml, 75-85 C heating and stirring dissolved, hot filter, the filtrate plus methanol 3000ml crystallization, filtration, filter cake with methanol amount of washing, collecting solid,At 40-50 under reduced pressure (vacuum ? 0.08MPa) dry 8h,A mixture of 1,2-bis [[N- [5- (4-bromophenyl)] - N'-propylsulfonamide-6-oxo] pyrimidinyl] ethyl dithioate was obtained in a yield of 76.5 %.

Reference： [1]Patent: CN106478522,2017,A .Location in patent: Paragraph 0042-0044; 0053-0055

26
[ 10305-42-7 ]
[ 147962-41-2 ]

Yield	Reaction Conditions	Operation in experiment
122.8 g	With ammonia; In dichloromethane; at 20℃; for 1h;Inert atmosphere;	Under the protection of nitrogen, 155 g of the compound of formula III was added to the clean four-necked reaction flask, 300 ml of dichloromethane was added,Stir,Temperature control at about 20 ,Slowly into the ammonia for about 1 hour,The reaction solution was concentrated under reduced pressure to obtain 132.5 g of the crude compound of formula V.The resulting crude compound was distilled to give 122.8 g of the compound of formula V as a colorless and transparent liquid. The total yield of the two steps was 88.8% (based on the compound of formula I). GC purity was 99.5%.

Reference： [1]Patent: CN107141238,2017,A .Location in patent: Paragraph 0029-0032; 0036-0039; 0043-0046; 0050-0053

27
[ 146533-41-7 ]
[ 147962-41-2 ]
[ 1393813-42-7 ]
C₁₆H₂₃BrN₆O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		A mixture of 1 (100 g, 0.33 mol), K2CO3 (221 g, 1.6 mol), and acetonitrile (1.3 L) washeated to 50C and stirred for 20 min. The solution of 2 (43 g, 0.31 mol) in acetonitrile(200 mL) was added dropwise and maintained at 50C for 10 h. The reaction solvent wasreplaced with toluene (2 L) using a Dean-Stark apparatus. The precipitated solid was filteredand suspended in water (2 L). The pH was adjusted to 7 by using 6 N hydrochloricacid and stirred for 20 min. The resulting precipitate was filtered and dried in the oven at55C for 5 h. The crude product was recrystallized from ethyl acetate to acquire 106 g(85%) of 3 as a white solid, mp 236C-238C. IR (KBr): 3272, 2966, 1593, 1566, 1438.1H NMR (500 MHz, DMSO-d6): d 0.73-0.76 (t, JD6.9, Me); 1.30-1.36 (m, CH2), 2.52-2.56 (m, CH2), 5.68-5.71 (t, JD6.6, NH), 7.12-7.14 (d, 2 H, ArH), 7.50-7.51 (d, 2 H,ArH), 8.04 (s, 1 H, ArH). 13C NMR (125 MHz, DMSO): d 12.41, 21.63, 45.75, 120.26,120.93, 131.50, 133.38, 136.21, 155.26, 156.73, 164.76.

Reference： [1]Organic Preparations and Procedures International,2017,vol. 49,p. 258 - 264

28
[ 147962-41-2 ]
N-(2-(difluoromethoxy)-6-methylpyridin-3-yl)-3-(2-isopropylphenyl)azetidine-3-carboxamide [ No CAS ]
N-(2-(difluoromethoxy)-6-methylpyridin-3-yl)-3-(2-isopropylphenyl)-1-(N-propylsulfamoyl)azetidine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere;	General procedure: To a solution of Ex 3 (50 mg, 0.12 mmol) and TEA (51 uL, 0.36 mmol) in dioxane (2 mL) is added sulfamide (12 mg, 0.12 mmol). The reaction mixture is stirred at 100C for 18 h and is then evaporated. The crude compound is purified by prep. HPLC (Prep HPLC 2) to give the title compound Ex 15-5 as a white solid (35 mg, 63% yield).

Reference： [1]Patent: WO2019/234115,2019,A1 .Location in patent: Page/Page column 55; 101-102

Same Skeleton Products

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Historical Records

Pharmaceutical Intermediates of
[ 147962-41-2 ]

Macitentan Intermediates

[ 706811-25-8 ]

5-(4-Bromophenyl)-6-hydroxypyrimidin-4(1H)-one

[ 146533-41-7 ]

5-(4-Bromophenyl)-4,6-dichloropyrimidine

[ 6313-33-3 ]

Formimidamide hydrochloride

[ 1878-68-8 ]

4-Bromophenylacetic acid

[ 41841-16-1 ]

Methyl 2-(4-bromophenyl)acetate

Macitentan Intermediates

[ 706811-25-8 ]

5-(4-Bromophenyl)-6-hydroxypyrimidin-4(1H)-one

[ 146533-41-7 ]

5-(4-Bromophenyl)-4,6-dichloropyrimidine

[ 6313-33-3 ]

Formimidamide hydrochloride

[ 1878-68-8 ]

4-Bromophenylacetic acid

[ 41841-16-1 ]

Methyl 2-(4-bromophenyl)acetate

Related Functional Groups of
[ 147962-41-2 ]

Aliphatic Chain Hydrocarbons

[ 1393813-41-6 ]

Potassium (N-propylsulfamoyl)amide

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[ CAS No. 147962-41-2 ] {[proInfo.proName]}

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[ 147962-41-2 ] Synthesis Path-Upstream 1~4

[ 147962-41-2 ] Synthesis Path-Downstream 1~28

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Macitentan Intermediates

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Aliphatic Chain Hydrocarbons

Amines

Sulfamides

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[ 147962-41-2 ]