Name: 54997-90-9|4-Isopropylbenzenesulfonyl chloride|96%
Brand: Ambeed
SKU: A880775
Rating: 90 (30 reviews)

1
[ 54997-90-9 ]
[ 4946-14-9 ]

Yield	Reaction Conditions	Operation in experiment
95.8%	With hydrogenchloride; sodium sulfide; iron; triphenylphosphine; In water; toluene; at 40℃; for 1h;	50.0 g of p-isopropylbenzenesulfonyl chloride, 100 ml of toluene, 100 ml of water and 90 ml of hydrochloric acid were added to the reaction vessel, mechanically stirred, and 0.7 g of triphenylphosphine, 2.3 g of iron powder and 18 g of sodium sulfide were added, and the reaction was carried out at 40 C. 1 hour,TLC tracking monitoring.The mixture was allowed to stand, the aqueous layer was separated, and the pH was adjusted to 1.5. After extraction, the organic phase was concentrated, and distilled under reduced pressure to give 33.5 g of p-isopropylthiophenol. The yield was 95.8%.

Reference： [1]Patent: CN108863870,2018,A .Location in patent: Paragraph 0019-0020; 0033-0034
[2]Synthesis,2009,p. 3211 - 3213
[3]Collection of Czechoslovak Chemical Communications,1974,vol. 39,p. 783 - 804
[4]Gazzetta Chimica Italiana,1993,vol. 123,p. 257 - 260
[5]Journal of Organic Chemistry,2006,vol. 71,p. 6248 - 6250

2
[ 98-82-8 ]
[ 54997-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid; In ice-water; chloroform;	(b) Synthesis of S-p-isopropylphenyl thioacetate To 300 ml of chloroform was added 80.0 g (0.67 mole) of isopropylbenzene and the mixture was stirred with cooling on an ice-bath at -10C - 0C. To this solution, 89 ml (1.34 moles) of chlorosulfonic acid, purified by distillation, was added dropwise over a period of about 30 minutes. After completion of dropwise addition, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured in ice-water and extracted with 200 ml of chloroform. The extract was washed 3 times with 500 ml portions of iced water and dried by addition of anhydrous magnesium sulfate. From this extract, the chloroform was distilled off under reduced pressure to give 55.0 g of p-isopropylbenzenesulfonyl chloride (yield based on isopropylbenzene: 38%).

Reference： [1]Canadian Journal of Chemistry,1985,vol. 63,p. 1150 - 1156
[2]Journal of Organic Chemistry,2006,vol. 71,p. 6248 - 6250
[3]Journal of Organic Chemistry,1988,vol. 53,p. 2367 - 2371
[4]Canadian Journal of Chemistry,1963,vol. 41,p. 483 - 494
[5]Gazzetta Chimica Italiana,1993,vol. 123,p. 257 - 260
[6]Patent: EP314042,1989,A3

3
[ 98-82-8 ]
[ 54997-90-9 ]
[ 16066-35-6 ]
[ 22033-07-4 ]
[ 61738-47-4 ]
[ 71530-58-0 ]
[ 22033-08-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 1695 - 1701
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1936 - 1942
[2]Journal of general chemistry of the USSR,1982,vol. 52,p. 341 - 343
Zhurnal Obshchei Khimii,1982,vol. 52,p. 390 - 393

4
[ 54997-90-9 ]
[ 6335-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran; water; at 0℃; for 4.11667h;	Preparation 12: 4-(1-methylethyl)benzenesulfonamide (P12) To concentrated aqueous ammonia (1.75 mL) in tetrahydrofuran (50 mL) at 0 0C with stirring was added over 2 min via syringe 4-(1-methylethyl)benzenesulfonyl chloride (3.3 g). A white precipitate was observed. Additional concentrated aqueous ammonia (1.75 mL) was added after 5 min. After 4 h volatiles were evaporated and the residue partitioned between EtOAc and aqueous NaHCO3. The organic layer was washed with brine, dried (Na2SO4) and volatiles evaporated to give the title crude compound as a colourless powder that was used without further purification.NMR (1H, CDCI3): delta 7.83 (d, 2H), 7.35 (d, 2H), 4.8 (bs, 2H), 2.95 (sept, 1 H), 1.25 (d, 6H).

Reference： [1]Canadian Journal of Chemistry,1963,vol. 41,p. 483 - 494
[2]Patent: WO2007/22935,2007,A1 .Location in patent: Page/Page column 38
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2267 - 2272
[4]International Journal of Biological Macromolecules,2018,vol. 115,p. 961 - 969
[5]Inorganica Chimica Acta,2019,vol. 486,p. 724 - 732

5
[ 54997-90-9 ]
[ 57493-24-0 ]
4-isopropyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With pyridine Ambient temperature;

Reference： [1]Röver, Stephan; Cesura, Andrea M.; Huguenin, Philipp; Kettler, Rolf; Szente, Andre [Journal of Medicinal Chemistry, 1997, vol. 40, # 26, p. 4378 - 4385]

6
[ 54997-90-9 ]
[ 15980-22-0 ]
<i>N</i>-(4-hydroxy-3,5-dimethyl-phenyl)-4-isopropyl-benzenesulfonamide [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 522 - 527

7
[ 16066-35-6 ]
[ 54997-90-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With phosphorus pentachloride In dichloromethane at 0℃; for 3h;

Reference： [1]Binisti, Carine; Assogba, Leon; Touboul, Estera; Mounier, Carine; Huet, Jack; Ombetta, Jean-Edouard; Dong, Chang Zhi; Redeuilh, Catherine; Heymans, Francoise; Godfroid, Jean-Jacques [European Journal of Medicinal Chemistry, 2001, vol. 36, # 10, p. 809 - 828]

8
[ 54997-90-9 ]
[ 103733-65-9 ]
(R)-2-(4-Isopropyl-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 781 - 788

9
[ 54997-90-9 ]
[ 521274-62-4 ]
1'-(adamantane-1-carbonyl)-[4,4']bipiperidinyl-1-carboxylic acid {2-hydroxy-3-[1-(4-isopropyl-benzenesulfonyl)-1<i>H</i>-indol-4-yloxy]-propyl}-isopropyl-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3461 - 3471

10
[ 54997-90-9 ]
[ 954369-11-0 ]
[ 954369-12-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine; at 20℃; for 19h;	61.4 4-lsopropyl-N-{2-methyl-6-[(1 -propionylpyrrolidin-3-yl)oxy]pyridin-3-yl}- benzenesulfonamide2-Methyl-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridin-3-amine (340 mg) was dissolved in pyridine (3.3 ml_) and <strong>[54997-90-9]4-isopropylbenzenesulfonyl chloride</strong> (358 mg) was slowly added under stirring. After 19 h stirring at room temperature, the reaction mixture was diluted with dichloromethane and 2 M aqueous NaOH was added. After stirring for 1 h at room temperature the phases were separated. The organic phase was dried (sodium sulfate), concentrated and the crude product purified by flash chromatography (silica, dichloromethane, 0.5 to 5 % methanol gradient). Yield: 460 mg (78 %, pale yellow oil).

Reference： [1]Patent: WO2007/118859,2007,A1 .Location in patent: Page/Page column 154

11
[ 54997-90-9 ]
[ 955378-56-0 ]
[ 1899-93-0 ]
[ 349-88-2 ]
[ 10130-74-2 ]
[ 1788-10-9 ]
[ 85-46-1 ]
[ 2991-42-6 ]
[ 10130-87-7 ]
[ 777-44-6 ]
[ 776-04-5 ]
[ 69360-26-5 ]
[ 16271-33-3 ]
[ 2888-06-4 ]
[ 98-59-9 ]
[ 98-68-0 ]
[ 93-11-8 ]
[ 121-60-8 ]
[ 133-59-5 ]
[ 2905-23-9 ]
1-(3,5-dichloropyridin-4-yl)-4-(3-methylphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(4-methylphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(2-methylphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(3-methoxyphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(4-methoxyphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(2-methoxyphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(4-propan-2-ylphenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(3-chlorophenyl)sulfonyl-4-(3,5-dichloropyridin-4-yl)-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-(4-fluorophenyl)sulfonyl-1,4-diazepane [ No CAS ]
1-(2-chlorophenyl)sulfonyl-4-(3,5-dichloropyridin-4-yl)-1,4-diazepane [ No CAS ]
2-[[4-(3,5-dichloropyridin-4-yl)-1,4-diazepan-1-yl]sulfonyl]benzonitrile [ No CAS ]
1-[4-[[4-(3,5-dichloropyridin-4-yl)-1,4-diazepan-1-yl]sulfonyl]phenyl]ethanone [ No CAS ]
1-(2,4-dichlorophenyl)sulfonyl-4-(3,5-dichloropyridin-4-yl)-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-naphthalen-1-ylsulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-naphthalen-2-ylsulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-[2-(trifluoromethyl)phenyl]sulfonyl-1,4-diazepane [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-[4-(trifluoromethyl)phenyl]sulfonyl-1,4-diazepane [ No CAS ]
N-[4-[[4-(3,5-dichloropyridin-4-yl)-1,4-diazepan-1-yl]sulfonyl]phenyl]acetamide [ No CAS ]
1-(3,5-dichloropyridin-4-yl)-4-[3-(trifluoromethyl)phenyl]sulfonyl-1,4-diazepane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Combinatorial reaction / High throughput screening (HTS);	Examples 1-19; General Method:; A solution of l-(3,5-dichloropyridin-4-yl)-l,4-diazepane (100 mg, 0.41 mmol) in DCM (1 ml) was added to the appropriate sulfonyl chloride (0.41 mmol) under a nitrogen atomosphere. DIPEA (0.22 ml, 1.22 mmol) was then added and the mixture stirred overnight at ambient temperature. The reaction mixtures were washed with water and the products isolated by <n="24"/>flash column chromatography (Combi-Flash Optix 10 on a 12g silica cartridge, eluting with a 1:1 mixture of EtOAc and isohexane) to give colourless solids.; The following compounds were synthesised as a multiparallel array:

Reference： [1]Patent: WO2007/122411,2007,A1 .Location in patent: Page/Page column 22-26

12
[ 54997-90-9 ]
4-(octahydropyrido[2,1-c][1,4]oxazin-3-yl)benzenamine [ No CAS ]
4-isopropyl-N-(4-(octahydropyrido[2,1-c][1,4]oxazin-3-yl)phenyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 20h;	4-lsopropylbenzenesulfonyl chloride (0.10Og, 0.46 mmol) in 2 mL acetonitrile was added to a stirring, solution of 4-octahydropyrido[2,1-c][1 ,4]oxazin-3-yl)benzenamine (0.100g,0.43 mmol) and diisopropylethyl amine (0.15 mL, 0.86 mmol) in 8 mL acetonitrile. This mixture was stirred at room temperature for 20 h, water was added and this was extracted into 50 mL EtOAc, dried (MgSO4) and concentrated to give a colorless oil (0.19g).LC/MS shows a trace starting material, mainly desired product and a minor amount of disulfonylated material. Purification by flash chromatography eluting with 50%-75% EtOAc/heptane yielded117 mg of the title compound as a colorless oil which slowly solidified to a waxy white solid. <n="31"/>HCI salt: NMR (MeOH-Cl4) delta 7.66 (d, J = 7.9 Hz, 2H), 7.31 (d, J = 7.9 Hz, 2H), 7.25 (d, J = 8.3 Hz, 2H), 7.11 (d, J = 7.9 Hz, 2H), 4.80 (d, J = 10.4 Hz, 1H), 4.10-4.04 (m, 1H), 3.73 (t, J = 11.8 Hz, 1 H), 3.66-3.30 (m, 3H), 3.09-3.00 (m, 2H), 2.91 (hept, J = 5.1 Hz, 1H), 1.98-1.80 (m, 5H), 1.70-1.53 (m, 2H), 1.19 (d, J = 7.1 Hz, 6H); 13C NMR (CDCI3) delta 154.5, 138.6, 137.3, 132.9, 128.7, 127.2, 127.1 , 127.0, 120.4, 75.4, 68.7, 62.2, 57.5, 54.4, 34.1 , 24.4, 22.9, 22.8, 21.5.

Reference： [1]Patent: WO2008/26046,2008,A1 .Location in patent: Page/Page column 29-30

13
[ 54997-90-9 ]
[ 1010384-44-7 ]
N-(4-(4-ethylmorpholin-2-yl)phenyl)-4-isopropylbenzenesulfonamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	4-lsopropylbenzenesulfonyl chloride (0.10 mL, 0.56 mmol) was added to a solution of 4-(4-ethylmorpholin-2-yl)benzenamine (0.109g, 0.528 mmol) and triethylamine (0.15 mL, 1.1 mmol) in CH2CI2 (10 mL) and stirred at room temperature overnight. Washed the reaction with sat NaHCO3, dried (MgSO4) and concentrated to a tan oil (287 mg). Purified by flash chromatography, eluting with 75% EtOAc/heptanes and EtOAc to afford the racemic title compound as a milky oil (106 mg.52%), which was converted to the HCI salt.NMR(MeOH-d4) delta 7.68 (d, J = 8.3 Hz, 2H), 7.34 (d, J = 8.3 Hz, 2H), 7.28 (d, J = 8.3 Hz, 2H), 7.14 (d, J = 8.7 Hz, 2H), 4.66 (dd, J = 11.2, 2.1 Hz, 1 H), 4.24 (dd, J = 13.7, 3.1 Hz, 1 H), 3.94 (dt, J = 12.6, 2.1 Hz, 1 H), 3.59-3.52 (m, 2H), 3.25-3.11 (m, 2H), 3.01-2.91 (m, 2H), 1.25-1.21 (m, 9H).LRMS m/z Calcd for C2iH28N2O3S, 388.2 , found, 389.0(M+H) (LCMS).

Reference： [1]Patent: WO2008/26046,2008,A1 .Location in patent: Page/Page column 31

14
[ 54997-90-9 ]
[ 1010384-44-7 ]
N-(4-(4-ethylmorpholin-2-yl)phenyl)-4-isopropylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In N,N-dimethyl-formamide; at 50℃; for 16h;	Examples 15-90; The following compounds were prepared using the following protocol:A 0.2 M stock solution of sulfonyl chloride (50 DL) in anhydrous DMF was added to a0.2 M solution of 4-(4-ethylmorpholin-2-yl)-benzenamine (50DL) in pyridine. The vessel was capped and heated at 5O0C for 16h, then the volatiles were removed under high vacuum.DMSO (300 DL) was added and the vessel was agitate for -30 min to dissolve the products.Additional DMSO was added to bring the volume to 1 mL. The sample was then purified byHPLC:Preparative Chromatography:Column: 19 x 50 Waters X-Bridge C-18, 5umFlow rate: 25 mL/min; Injection volume: 900 uL in DMSO (10-30 mg)Solvents: A: Water; B: Acetonitrile; C: 1% aq. TFA; D: 1% aq. ammonium hydroxideGradients: Determined based on retention time in pre-purification analyses:

Reference： [1]Patent: WO2008/26046,2008,A1 .Location in patent: Page/Page column 41; 42

15
[ 54997-90-9 ]
[ 848636-35-1 ]
4-isopropyl-N-{4-[6-(2-methoxy-phenyl)-pyrimidin-4ylamino]-phenyl}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 60h;	To a mixture of N- [6- (2-METHOXY-PHENYL)-PYRIMIDIN-4-YL]-BENZENE-1, 4-diamine (0. 229mmol) in CH2CI2 (6mL) COOLED TO ~0C under nitrogen atmosphere, Et3N (0. 274mmol) was added followed by the sulfonyl chloride (0. 252mmol). The mixture was allowed to warm to room temperature and then stirred for 60h. The solvent was evaporated under reduced pressure, the residue suspended in water and extracted with EtOAc (3x). Combined extracts were dried (MGS04) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography to afford the product.

Reference： [1]Patent: WO2005/26129,2005,A1 .Location in patent: Page/Page column 99

16
[ 54997-90-9 ]
[ 773879-29-1 ]
[ 773878-59-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In tetrahydrofuran; at 20℃;	1.4 g (7.97 mmol) of 6-(4-allylpiperazin-1-yl)pyridin-3-ylamine from Example 1.2 and 1.74 g (7.97 mmol) of <strong>[54997-90-9]4-isopropylbenzenesulfonyl chloride</strong> were dissolved in 30 ml of tetrahydrofuran at room temperature. 3.3 ml (23.91 mmol) of triethylamine were then added to this mixture. After that, the reaction mixture was stirred overnight at room temperature. After the solvent had been evaporated to dryness, water was added to the residue. The aqueous reaction mixture was made acid with 1N hydrochloric acid and extracted twice with diethyl ether. After that, the aqueous phase was made alkaline (pH 9-10) with a 1N aqueous solution of sodium hydroxide and then extracted twice with diethyl ether. After the combined organic phases had been dried over sodium sulfate, the drying agent had been filtered off and the solvent had been evaporated down to dryness, the resulting residue was chromatographed on silica gel using cyclohexane/ethyl acetate (45:55% to 100% ethyl acetate). The filtrate was evaporated down to dryness. The resulting residue was thoroughly stirred in 10 ml of heptane, filtered off in suction and dried, with 1.93 g (61% of theory) of the title compound being obtained. 1H-NMR (500 MHz, CDCl3): delta [ppm] 7.7 (s, 1H); 7.6 (d, 2H); 7.4 (d, 1H); 7.3 (d, 2H); 6.6 (d, 1H); 6.4 (bs, 1H); 5.9 (m, 1H); 5.2 (m, 2H); 3.5 (m, 4H); 3.1 (m, 2H); 3.0 (m, 1H); 2.5 (m, 4H); 1.2 (d, 6H). MS [m+1]: 401.

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 25

17
[ 54997-90-9 ]
[ 773879-32-6 ]
N-[6-(4-allyl-3-methylpiperazin-1-yl)pyridin-3-yl]-4-isopropylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	305 mg (1.31 mmol) of 6-(4-allyl-3-methylpiperazin-1-yl)pyridin-3-ylamine from Example 13.3 and 301 mg (1.38 mmol) of <strong>[54997-90-9]4-isopropylbenzenesulfonyl chloride</strong> were dissolved in 10 ml of tetrahydrofuran at room temperature, after which 0.55 ml (3.94 mmol) of triethylamine was added dropwise. After that, the reaction mixture was stirred overnight at room temperature. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and the mixture was made acid with 1N hydrochloric acid and extracted twice with diethylether. The aqueous phase was made alkaline, to pH 9-10, using a 1N aqueous solution of sodium hydroxide and then extracted twice with diethyl ether. After the combined organic phases had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was purified by column chromatography (cyclohexane/ethylacetate from 50:50 to 20:80). After that, the filtrate was evaporated down to dryness. The resulting residue was converted into the hydrochloride using ethereal hydrochloric acid, with 417 mg (74% of theory) of the title compound being obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm] 11.3 (bs, 1H); 10.0 (s, 1H); 7.8 (d, 1H); 7.6 (d, 2H); 7.4 (d, 2H); 7.3 (d, 1H); 6.9 (d, 1H); 6.0 (m, 1H); 5.5 (m, 2H); 4.3 (m, 1H); 4.0 (m, 1H); 3.7 (m, 1H); 3.4 (m, 1H); 3.2 (m, 3H); 3.0 (m, 3H); 1.4 (d, 3H); 1.2 (d, 6H). MS [m+1]: 415 (free base).

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 27-28

18
[ 54997-90-9 ]
[ 773879-34-8 ]
N-[5-(4-allylpiperazin-1-yl)pyridin-2-yl]-4-isopropylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20 - 50℃; for 6h;	520 mg (2.38 mmol) of 5-(4-allylpiperazin-1-yl)pyridin-2-ylamine and 495 mg (2.26 mmol) of <strong>[54997-90-9]4-isopropylbenzenesulfonyl chloride</strong> were dissolved in 5 ml of tetrahydrofuran at room temperature, after which 1.0 ml (7.15 mmol) of triethylamine was added dropwise and the mixture was stirred at 40-50 C. for 6 hours. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and this mixture was made acid using 1N aqueous hydrochloric acid and extracted twice with diethyl ether. The aqueous phase was made alkaline, to pH 9-10, using a 1N aqueous solution of sodium hydroxide and then extracted twice with ethyl acetate. After the combined organic phases had been dried over sodium sulfate, the drying agent had been filtered off and the solvent had been evaporated down to dryness, the resulting residue was chromatographed on silica gel using ethyl acetate. After the solvent had been removed, the resulting residue was brought into solution using a little diethyl ether in dichloromethane and then converted into the hydrochloride using ethereal hydrochloric acid. 415 mg (44% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm] 11.6 (bs, 1H); 7.9 (d, 1H); 7.8 (d, 2H); 7.5 (dd, 1H); 7.4 (d, 2H); 7.1 (d, 1H); 6.0 (m, 1H); 5.5 (m, 2H); 3.7 (m, 4H); 3.4 (m, 2H); 3.1 (m, 4H); 3.0 (m, 1H); 1.2 (d, 6H). 13C-NMR (100 MHz, DMSO-d6): delta [ppm] 153.3 (C); 144.5 (C); 141.6 (C); 138.4 (C); 134.3 (CH); 127.3 (CH); 127.0 (CH); 126.8 (CH); 124.8 (CH2); 113.8 (CH); 57.3 (CH2); 49.6 (CH2); 45.2 (CH2); 33.3 (CH); 23.4 (CH3). MS [m+1]: 401.

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 29

19
[ 54997-90-9 ]
[ 773879-36-0 ]
[ 773878-74-3 ]

Yield	Reaction Conditions	Operation in experiment
18%	With triethylamine; In tetrahydrofuran; at 20℃;	216 mg (0.98 mmol) of 2-(4-Allylpiperazin-1-yl)pyrimidin-5-ylamine from Example 16.2 and 215 mg (0.98 mmol) of <strong>[54997-90-9]4-isopropylbenzenesulfonyl chloride</strong> were dissolved in 20 ml of tetrahydrofuran at room temperature, after which 0.4 ml (3.0 mmol) of triethylamine was added dropwise and the mixture was stirred at room temperature overnight. After the solvent had been evaporated down to dryness, water was added to the resulting residue. The aqueous reaction mixture was made acid using 1N aqueous hydrochloric acid and extracted twice with diethyl ether. The aqueous phase was made alkaline to pH 9-10, using a 1N solution of sodium hydroxide and then extracted three times with diethyl ether. The combined organic phases were dried over sodium sulfate. The residue which was obtained after filtering off the drying agent and evaporating the solvent down to dryness was thoroughly stirred with a mixture composed of heptane and diethyl ether, filtered off with suction and dried, with 71 mg (18% of theory) of the title compound being obtained. 1H-NMR (500 MHz, CDCl3): delta [ppm] 8.0 (s, 2H); 7.7 (d, 2H); 7.3 (d, 2H); 6.2 (bs, 1H); 5.9 (m, 1H); 5.2 (m, 2H); 3.8 (m, 4H); 3.1 (m, 2H); 3.0 (m, 1H); 2.5 (m, 4H); 1.3 (d, 6H). MS [m+1]: 402.

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 29

20
[ 54997-90-9 ]
[ 898839-54-8 ]
C₂₂H₃₀N₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; In dichloromethane;	Reaction of 0.300 g of 6-(4-allylpiperazin-1-yl)-2-methylpyridin-3-amine (1.29 mmol) and 0.282 g of 4-isopropylbenzene-1-sulfonyl chloride (1.29 mmol) in 10 ml of a mixture of pyridine and dichloromethane (1:2) yielded 0.465 g (87%) of the title compound as a white solid. The title compound was onverted into the fumarate salt in methanol by addition of fumaric acid. MS [m+1]: 415 1H-NMR (400 MHz, CH3OD): delta [ppm]: 7.6 (d, 2H), 7.5 (d, 2H), 7.3 (m, 1H), 7.2 (m, 1H), 7.1 (d, 1H), 6.5 (d, 1H), 5.9 (m, 1H), 5.4 (m, 2H), 3.5 (m, 5H), 3.0 (m, 4H), 2.8 (m, 2H), 1.9 (s, 3H), 1.2 (m, 6H).

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 31

21
[ 54997-90-9 ]
[ 41288-96-4 ]
[ 898839-75-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In tetrahydrofuran; at 20℃; for 2h;	Example 59 4-Isopropyl-benzenesulfonic acid 6-(4-allyl-piperazin-1-yl)-pyridin-3-yl ester 59.1 4-Isopropyl-benzenesulfonic acid 6-chloro-pyridin-3-yl ester A reaction flask containing 500 mg of 6-chloropyridin-3-ol (3.86 mmol) and 844 mg of 4-isopropyl-benzenesulfonylchloride (0.20 mmol) in dry tetrahydrofurane (10 ml) was flushed with N2. 1.6 ml of triethylamine were added and the reaction mixture was stirred at room temperature for 2 h. Thereby 4-isopropyl-benzenesulfonic acid 6-chloro-pyridin-3-yl ester ester was obtained in 98% yield. MS [m+1]: 312 1H-NMR (400 MHz, DMSO-d6): delta [ppm] 8.1 (d, 1H); 7.8 (d, 2H); 7.6 (m, 4H); 3.0 (m,1H); 1.2 (d, 6H).

Reference： [1]Patent: US2006/160809,2006,A1 .Location in patent: Page/Page column 33

22
[ 54997-90-9 ]
[ 5307-14-2 ]
[ 883902-43-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With N,N-dimethyl-aniline; In acetonitrile; at 0 - 20℃; for 18h;	To a mixture of 2-nitro-benzene-1 ,4-diamine (10g, 65.30 mmol) and N1N- dimethylaniline (8.7 g, 71.83 mmol) in acetonitrile (310 ml) at 00C 4-isopropyl- benzenesulfonylchloride (13.85 g, 63.34 mmol) was added over a period of 1 h. The mixture was stirred at O0C for 1h and for 16 h at room temperature. After concentrating the mixture in vacuo the obtained oil was triturated with water. The precipitate was col¬ lected, washed with ethanol and dried in vacuo to give the product as a yellow powder (11.76 g, 54%).

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 104

23
[ 54997-90-9 ]
[ 883993-15-5 ]
[ 883993-16-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine; at -5 - 20℃; for 18h;	To a solution of (5-amino-pyridin-2-yl)-acetonitrile (1 g, 7.5 mmol) in pyridine (10 ml) 4- Isopropyl-benzenesulfonyl chloride (1.64 g, 7.5 mmol) was added at -5-00C. The mix¬ ture was stirred at O0C for 2 h and at room temperature for 16 h. The mixture was con¬ centrated under reduced pressure, and the residue partitioned between ethyl acetate and saturated aqueous NaHCO3. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with water, and brine, dried over MgSO4, filtered, and the solvent evaporated under reduced pressure to give the product as a brown oil which was purified by column chromatography using methyl- tert-butylether as an eluent to give a colorless oil (1.7 g, 72%).MS (ESI) m/z: 316.10 [M+H]+

Reference： [1]Patent: WO2006/40179,2006,A1 .Location in patent: Page/Page column 115

24
[ 54997-90-9 ]
[ 883901-92-6 ]
[ 883901-52-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In tetrahydrofuran; at 10 - 20℃; for 16h;	To a solution of 3-(3-amino-phenyl)-pyrrolidine-1-carboxylic acid methyl ester (500 mg, 2.27 mmol) and triethylamine (500 mg, 4.94 mmol) in THF (20 ml) at 1O0C 4-isopropyl- benzenesulfonylchloride (500 mg, 2.27 mmol) was added. The mixture was allowed to come to room temperature and was stirred for 16 h. The mixture was poured into water and extracted three times with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over MgSO4 and evaporated under re¬ duced pressure to give the product as a brown oil (1 g, 100%).

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 130

25
[ 54997-90-9 ]
[ 883901-77-7 ]
[ 883901-78-8 ]

Yield	Reaction Conditions	Operation in experiment
21%	With triethylamine; In tetrahydrofuran; at 20 - 150℃;Heating / reflux; Microwave (CEM);	4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenylamine (400 mg, 1.48 mmol) and 4-isopropyl- phenylsulfonyl chloride (324 mg, 1.48 mmol) were dissolved in tetrahydrofuran (25 ml). Triethylamine (0.62 ml, 4.44 mmol) was added and the reaction mixture stirred over night at room temperature (10 % conversion) and subsequently refluxed for 4 h (30 % conversion). Small portions of 4-isopropyl-phenylsulfonyl chloride and triethylamine were added and the reaction mixture was stirred 15 min at 150 0C in the microwave (CEM). This procedure was repeated until complete conversion was observed. The solvent was evaporated under reduced pressure, the residue treated with ethyl acetate (50 ml) and extracted twice with slightly acidic water. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give an oil (170 mg, 21 %). ESI-MS: 453.1 [M+H]+

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 166-167

26
[ 54997-90-9 ]
[ 883901-82-4 ]
[ 883901-83-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine; In tetrahydrofuran; at 20 - 150℃;Heating / reflux; Microwave (CEM);	4-(1-Benzyl-pyrrolidin-3-yl)-2-methoxy-phenylamine (220 mg, 0.78 mmol) and 4- isopropylphenylsulfonyl chloride (170 mg, 0.78 mmol) were dissolved in tetrahydrofuran (20 ml). Triethylamine (0.32 ml, 2.34 mmol) was added and the reaction mixture stirred over night at room temperature (10 % conversion) and subsequently refluxed for 4 h (70 % conversion). One small portion of <strong>[54997-90-9]4-isopropylphenylsulfonyl chloride</strong> and triethyl¬ amine were added and the reaction mixture was stirred 15 min at 150 0C in the micro- wave (CEM). The solvent was evaporated under reduced pressure, the residue treated with ethyl acetate (50 ml) and extracted twice with slightly acidic water. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give an oil (470 mg). The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (gradient 0 - 100 %). Fractions con- taining the product were combined, the solvent evaporated to yield an oil (143 mg, 40 %). ESI-MS: 465.1 [M+H]+

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 169

27
[ 54997-90-9 ]
[ 883901-85-7 ]
4-isopropyl-N-[4-(1-propyl-piperidin-3-yl)-phenyl]-benzenesulfonamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		4-(1-Propyl-piperidin-3-yl)-phenylamine (600 mg, 1.65 mmol) and 4-isopropyl- phenylsulfonyl chloride (397 mg, 1.81 mmol) were dissolved in tetrahydrofuran (25 ml). Triethylamine (760 mul, 5.44 mmol) was added and the reaction mixture stirred for 72 hours at room temperature. The solvent was evaporated under reduced pressure, the residue treated with diethyl ether (50 ml) and three times extracted with water (3 x 30 ml). The organic phase was treated with 1 molar HCI solution. The acidic aqueous so¬ lution was made alkaline with NaOH solution to pH 9-10 and then extracted with ethyl acetate (25 ml). The organic phase was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product (580 mg). The crude product was purified via silica gel chromatography with ethyl acetate. Fractions containing the product were combined, the solvent evaporated to yield the pure product which was then converted into the hydrochloride salt via adding a solution of 1 N HCI in diethyl ether. The precipitate was filtered off and dried in vacuo to give the pure product (283 mg, 39 %). ESI-MS: 401.15 [M+H]+1H-NMR (DMSO-de, 400 MHz): delta [ppm] 10.3 (s, 1H), 10.25 (bs, 1H), 7.7 (d, 2H), 7.45 (d, 2H), 7.15 (d, 2H), 7.1 (d, 2H), 3.45 (m, 1H), 3.35 (m, 1H), 3.1-2.8 (m, 6H), 1.9 (m, 2H)1 1.85 (m, 1H), 1.75 (m, 2H), 1.55 (m, 1H), 1.2 (d, 6H), 0.9 (t, 3H).

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 172

28
[ 54997-90-9 ]
C₁₁H₁₅N₃O [ No CAS ]
4-isopropyl-N-[6-(1-propionyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃;	1-[3-(5-nitro-pyridin-2-yl)-azetidin-1-yl]-propan-1-one (340 mg, 1.44 mmol) was dis¬ solved in ethanol (EtOH) (25 ml) and SnCI2.2H2O (1.63 g, 7.22 mmol) was added. The resulting mixture was refluxed for 8 h and the solvent next removed under vacuum. The raw material was dissolved in ethyl acetate and washed successively with 2N aqueous NaOH (x2) and water. The organic layer was dried (Na2SO4), filtered through a pad of celite and evaporated. Half of the crude material was then dissolved in CH2CI2 (40 ml) and pyridine (115 mul, 1.41 mmol) followed by 4-isopropylbenzensulfonylchloride (190 mul, 1.05 mmol) were added dropwise. After stirring at room temperature overnight, the re¬ action mixture was diluted with CH2CI2 and washed successively with 1 N aqueous HCI, saturated aqueous NaHCO3 and water. The organic layer was dried (Na2SO4) and evaporated. The residue was chromatographied on silica gel (heptane:ethyl acetate, 1 :3) to afford the title compound (150 mg, 54% for two steps) as a light yellow oil. MS (ESI+) m/z = 388.1 [M+H]+ EPO <DP n="136"/>1H NMR (400 MHz, CDCI3) : delta (ppm) 1.14 (t, J = 7.5 Hz, 3H), 1.24 (d, J = 6.9 Hz, 6H)1 2.14 (q, J = 7.5 Hz, 2H), 2.94 (m, 1 H), 3.87 (m, 1H), 4.10 (dd, J = 9.7, 5.9 Hz, 1 H), 4.34 (m, 2H), 4.42 (t, J = 8.5 Hz, 1 H), 7.12 (d, J = 8.4 Hz, 1 H), 7.31 (m, 3H), 7.59 (dd, J = 8.4, 2.6 Hz, 1 H), 7.71 (d, J = 8.4 Hz, 2H), 8.25 (d, J = 2.3 Hz, 1 H).

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 134-135

29
[ 54997-90-9 ]
[ 883901-38-0 ]
4-isopropyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		0.4 g of (S)-3-(4-amino-phenyl)-1 -propyl-pyrrolidine (1.96 mmol) and 0.407 mg of 4- isopropyl-phenylsulfonyl chloride (1.86 mmol) were dissolved in 15 ml of tetrahydrofu- ran. 0.82 ml of triethylamine (5.87 mmol) were added and the reaction mixture stirred for 15 h at room temperature. The solvents were evaporated under reduced pressure, the residue treated with water and adjusted to an alkaline pH with sodium hydroxide solution. The aqueous layer was extracted three times with diethyl ether, the organic layers combined, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified with silica gel chromatography with ethyl acetate/methanol (2.5-3%) as eluent, yielding 0.225 g of the purified product. This material was dissolved in 15 ml of diethyl ether and 1 ml of dichloromethane, 0.61 ml of 1 N HCI in diethyl ether added, and after formation of a precipitate, the suspen¬ sion evaporated under reduced pressure to yield 0.235 g of a white precipitate. ESI-MS: 387.2 [M+H]+ 1H-NMR (DMSO-d6): delta [ppm] 11.3 and 11.1 (2 s, broad, 1 H), 10.35 (m, 1 H), 7.7 (d, 2H), 7.4 (d, 2H), 7.15-7.3 (m, 2H), 7.1 (m, 2H), 3.2-3.8 (several m, 4H), 2.85-3.15 (several m, 4H), 2.3 (m, 1H), 1.8-2.0 (m, 1 H), 1.6-1.75 (m, 2H), 1.15 (d, 6H), 0.9 (m, 3H).

Reference： [1]Patent: WO2006/40182,2006,A1 .Location in patent: Page/Page column 109-110

30
[ 54997-90-9 ]
[ 883902-48-5 ]
N-[5-(4-isopropyl-benzenesulfonylamino)-indan-2-ylmethyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; In dichloromethane; at 5℃; for 3h;	N-(5-Amino-indan-2-ylmethyl)-propionamide (0.93 g, 4.26 mmol) was dissolved in pyri- dine-dichloromethane (1 :2, 60 ml_) and cooled to 5C. 4-lsopropylbenzenesulfonyl chloride (0.98 g, 4.48 mmol) was added and the solution stirred at 5C for 3 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give the product as a brown oil (1.69 g, 99%). MS (ESI) m/z: 401.1 [M+H]+

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 107-108

31
[ 54997-90-9 ]
[ 883902-51-0 ]
[ 883902-52-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; In dichloromethane; at 5℃; for 3h;	N-(4-Amino-indan-2-ylmethyl)-propionamide (0.51 g, 2.34 mmol) was dissolved in pyri- dine-dichloromethane (1 :2, 30 mL) and cooled to 5C. 4-lsopropylbenzenesulfonyl chloride (0.54 g, 2.47 mmol) was added and the solution stirred at 5C for 3 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give the product as a brown oil (0.95 g, 100%). MS (ESI) m/z: 401.1 [M+H]+

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 109

32
[ 54997-90-9 ]
[ 883902-54-3 ]
N-[5-(4-isopropyl-benzenesulfonylamino)-indan-1-ylmethyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	With tri-tert-butyl phosphine; sodium hydride;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 150℃; for 1.5h;Microwave irradiation;	N-(5-Bromo-indan-1-ylmethyl)-propionamide (280 mg, 0.99 mmol) was dissolved in THF (5 mL) and tris(dibenzylideneacetone)dipalladium (45 mg, 0.05 mmol) and tri-t- butylphosphine (10 mg, 0.05 mmol) added under N2 atmosphere. A solution of 4- isopropylbenzenesulfonyl chloride (198 mg, 0.99 mmol) and NaH (52 mg, 50% in oil) was added and the solution stirred at 1500C for 1.5 h in a microwave.Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and separated by preparative HPLC (20-95% MeOH) to give the 2 isomeric amino products and a mixed fraction (92 mg, 22%). The product was obtained as a colorless oil (21 mg, 5%).

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 111

33
[ 54997-90-9 ]
[ 883902-59-8 ]
[ 883942-92-5 ]

Yield	Reaction Conditions	Operation in experiment
	With polystyrene-bound DMAP; In tetrahydrofuran; at 150 - 160℃; for 12h;Microwave irradiation;	6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1 H-benzo[e]isoindol-7-yl-amine (100 mg, 0.33 mmol) and polystyrene-bound DMAP (4-(N,N-dimethylamino)pyridine) (loa- ding 1.06 mmol/g, 32 mg) were treated with tetrahydrofuran (10 ml). Subsequently iso- propylphenylsulfonyl chloride (73 mg, 0.33 mmol) was added and stirred for 5 hours at 150 0C in the microwave (CEM). Another portion of isopropylphenylsulfonyl chloride EPO <DP n="116"/>and polystyrene-bound DMAP was added and stirring continued for 7 hours at 160 0C in the microwave. The solvent was evaporated under reduced pressure, the residue treated with water (30 ml) and twice extracted with ethyl acetate (2 x 30 ml). The or¬ ganic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give an oil (470 mg). The crude product was purified via HPLC chromatography. Fractions containing the product were combined and the sol¬ vent evaporated. The residue was converted into the hydrochloride salt (4 mg, 2 %). ESI-MS: 481.15/483.15 [M+H]+1H-NMR (DMSO-d6, 400 MHz): delta [ppm] 10.4 (bs, 1 H), 9.95 (s, 1 H), 7.7 (d, 2H), 7.45 (m, 3H), 4.1 (m, 0.5H), 3.85 (m, 0.5H), 3.7 (m, 0.5H), 3.55 (m, 0.5H), 3.45 (m, 1H), 3.1 (m, 2H), 3.0 (sept, 1 H), 2.95-2.55 (m, 5H), 1.85 (m, 1 H), 1.65 (m, 3H), 1.2 (d, 6H), 0.9 (t, 3H).

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 114-115

34
[ 54997-90-9 ]
[ 883902-60-1 ]
[ 883942-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	2-Propyl-2,3,3a,4,5,9b-hexahydro-1 H-benzo[e]isoindol-7-yl-amine (40 mg, 0.17 mmol) and <strong>[54997-90-9]4-isopropylphenylsulfonyl chloride</strong> (38 mg, 0.17 mmol) were dissolved in tetra- hydrofuran (20 ml). Triethylamine (70 mul, 0.52 mmol) was added and the reaction mix¬ ture stirred over night at room temperature. The solvent was evaporated under reduced pressure, the residue treated with water (30 ml) and ethyl acetate (30 ml). The aqueous EPO <DP n="117"/>phase was once more extracted with ethyl acetate and the combined organic phases were dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product (120 mg). The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (gradient 0 - 100 %). Fractions containing the product were combined and the solvent evaporated to yield the pure product which was converted into its hydrochoride salt (15 mg, 18 %). ESI-MS: 413.2 [M+H]+1H-NMR (DMSOd6, 400 MHz): delta [ppm] 10.4 (bs, 1 H), 10.2 (s, 1 H), 7.7 (d, 2H), 7.45 (d, 2H), 7.05 (d, 1 H), 6.95 (d, 1 H), 6.9 (m, 2H), 3.9 (m, 1 H), 3.4 (m, 2H), 3.05 (m, 2H), 2.95 (sept, 1 H), 2.8 (m, 1 H), 2.6 (m, 4H), 1.65 (m, 4H), 1.2 (d, 6H), 0.9 (t, 3H).

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 115-116

35
[ 54997-90-9 ]
[ 883902-38-3 ]
[ 883902-39-4 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	With pyridine; at 20℃; for 16h;	To a solution of 5-amino-1 H-indole-2-carboxylic acid propylamide (500 mg, 2.3 mmol) in pyridine (20 ml) 4-isopropyl-benzenesulfonyl chloride (500 mg, 2.3 mmol) was added. The mixture was stirred at room temperature for 16 h. After evaporation of the solvent the residue was partitioned between ethyl acetate and saturated aqueous Na- HCO3. The organic layer was separated, washed with saturated aqueous NaHCO3 and dried over MgSO4. The flitered solution was evaporated to give the product as a yellow powder (91 Omg, 98.8%). MS (ESI) m/z: 400.01 [M+H]+

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 100

36
[ 54997-90-9 ]
[ 883902-41-8 ]
N-[6-(4-isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; at 0 - 20℃; for 17h;	To a solution of N-(6-amino-1 ,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-propionamide (290 mg, 1.26 mmol) in pyridine (10 ml) at O0C 4-isopropyl-benzenesulfonyl chloride (280 mg, 1.26 mmol) waps added. The mixture was stirred at 00C for 1 h and 16 h at room temperature. After evaporation under reduced pressure the obtained residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed twice with saturated aqueous NaHCO3, dried over MgSO4, filtered and the solvent evaporated under reduced pressure to give the product as a brown resin (530 mg, 100%). MS (ESI) m/z: 415.15 [M+H]+

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 103

37
[ 54997-90-9 ]
[ 884306-43-8 ]
(R)-N-[7-(4-isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In pyridine; dichloromethane; at 5℃; for 3h;	1.4 (R)-N-[7-(4-lsopropyl-benzenesulfonylamino)-1 ,2,3,4-tetrahydro-naphthalen-2-yl]- propionamide; (R)-N-(7-Amino-1 ,2,3,4-tetrahydro-naphthalen-2-yl)-propionamide (0.34 g, 1.56 mmol) was dissolved in pyridine-dichloromethane (1 :2, 30 ml_) and cooled to 5C. 4-lsopropylbenzenesulfonyl chloride (0.37 g, 1.69 mmol) was added and the solution stirred at 5C for 3h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give the product as a yellow oil (0.56 g,90%). 7-Amino: MS (ESI) m/z: 401.1 [M+H]+

Reference： [1]Patent: WO2006/40178,2006,A1 .Location in patent: Page/Page column 93

38
[ 54997-90-9 ]
[ 884306-44-9 ]
(R)-N-[5-(4-isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In pyridine; dichloromethane; at 5℃; for 3h;	EXAMPLE 4; (R)-N-[5-(4-lsopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]- propionamide; The 5-amine isomer (0.26 g, 1.19 mmol) from 1.3 was dissolved in pyridine- dichloromethane (1 :2, 30 mL) and cooled to 5C. 4-lsopropylbenzenesulfonyl chloride (0.29 g, 1.31 mmol) was added and the solution stirred at 50C for 3h. So¬ li itinn was evaoorated. partitioned between ethyl acetate and water, and the or- EPO <DP n="96"/>ganic phase separated and dried over MgSO4. The filtered solution was concen¬ trated to give the product as a yellow oil (0.61 g, 100%). MS (ESI) m/z: 401.1 [M+H]+

Reference： [1]Patent: WO2006/40178,2006,A1 .Location in patent: Page/Page column 94-95

39
[ 54997-90-9 ]
[ 884307-00-0 ]
N-[3-(benzyl-propyl-amino)-chroman-7-yl]-4-isopropyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With dmap; In tetrahydrofuran; at 20℃;	71.11 N-[3-(Benzyl-propyl-amino)-chroman-7-yl]-4-isopropyl-benzenesulfonamide; N-3-Benzyl-N-3-propyl-chroman-3,7-yl-diamine (110 mg, 0.13 mmol) was dis- solved in tetrahydrofuran (5 ml). Subsequently, dimethylaminopyridine (17 mg,0.13 mmol) and 4-isopropyl-benzenesulfonyl chloride (57 mg, 0.26 mmol) were added and the reaction mixture stirred was over night at room temperature. The solvent was evaporated under reduced pressure, the residue treated with water and diethyl ether. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product(2.5 g). The crude product was purified by chromatography on silica gel using di- chloromethane/methanol (100:0 to 0:100) as eluent, yielding the purified product (25 mg, 40 %). ESI-MS: 479.25 [M+H]+

Reference： [1]Patent: WO2006/40178,2006,A1 .Location in patent: Page/Page column 140

40
[ 54997-90-9 ]
[ 883993-08-6 ]
[ 883992-82-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With pyridine; In dichloromethane; at 5℃; for 18h;	2-(4-Aminobenzyl)-1-propylpyrrolidine (300 mg, 1.37 mmol) was dissolved in pyridine- dichloromethane (1 :2, 9 mL) and cooled to 50C. 4-lsopropylbenzenesulfonyl chloride (300 mg, 0.24 mmol) was added and the solution stirred at 5C for 18 h. The solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and sepa- rated by column chromatography (dichloromethane-2% methanol) to give an oil. The oil was dissolved in ethyl acetate and HCI (4M, dioxane) was added to give the product as a white solid (180 mg, 30%).MS (ESI) m/z: 401.5 [M+H]+ 1H-NMR (DMSOd6): delta [ppm] 10.52 (s, 1 H), 7.67 (d, 2H), 7.38 (d, 2H), 7.18 (d, 2H),7.04 (d, 1H), 3.52 (m, 1 H), 3.43 (m, 1H), 3.24 (m, 1 H), 3.10-2.75 (m, 5H), 1.82 (m,3H), 1.62 (m, 3H), 1.15 (d, 6H), 0.82 (t, 3H).13C-NMR (DMSOd6): delta [ppm] 153.5 (s), 137.2 (s), 136.5 (s), 132.6 (s), 129.7 (d), 127.1(d), 126.7 (d) 119.9 (d), 68.1 (d), 54.5 (t), 52.8 (t), 35.2 (t), 33.2 (d), 29.1 (t), 26.8 (t), 23.3 (q), 21.1 (t), 18.2 (t), 11.0 (q).

Reference： [1]Patent: WO2006/40179,2006,A1 .Location in patent: Page/Page column 117

41
[ 54997-90-9 ]
[ 883994-19-2 ]
[ 883994-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 18h;	0.58 g of ((R)-5-amino-indan-2-yl)-propyl-carbamic acid tert-butyl ester (2.0 mmol) were dissolved in 20 ml of tetrahydrofuran and 0.393 mg of 4-isopropyl- benzenesulfonylchloride (1.8 mmol) and 0.83 ml of triethylamine (6 mmol) added. After stirring for 18 h at room temperature, the solvent was evaporated under re¬ duced pressure, the remaining material partitioned between diethyl ether and wa- ter, the aqueous layer reextracted with diethylether, and the combined organic layers dried over magnesium sulfate, filtered, and the solvent evaporated. The crude material was purified via silica gel chromatography with cyclohexane-ethyl acetate (12.5 %) as eluent. Fractions combining the product were combined and the solvent removed under reduced pressure to yield 0.584 g of product. ESI-MS: 495.2 [M+Na]+ , 417.1 [M-tBu+H]+ , 373.1 [M-Boc+H]+

Reference： [1]Patent: WO2006/40177,2006,A1 .Location in patent: Page/Page column 95

42
[ 54997-90-9 ]
trans-2,3,4,4a,9,9a-hexahydro-1-propyl-1H-indeno[2,1-b]pyridin-7-amine [ No CAS ]
4-isopropyl-N-((4aS,9aS)-1-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl)-benzenesulfonamide [ No CAS ]
4-isopropyl-N-((4aR,9aR)-1-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%; 2%	With pyridine; In dichloromethane; at 5℃; for 18h;	The mixture of amines (200 mg, 0.87 mmol) was dissolved in pyridine- dichloromethane (1 :2, 15 ml) and cooled to 5C. 4-lsopropylbenzenesulfonyl chloride (200 mg, 0.91 mmol) was added and the solution stirred at 5C for 18h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was con¬ centrated and separated by preparative chiral HPLC (20-95% methanol) to give the pure (RR) and (SS) products and a mixed fraction (92 mg, 22%). The 1st pro¬ duct was obtained as a colorless oil (21 mg, 5%) and is 4-isopropyl-N- ((4aS,9aS)-1-propyl-2,3,4,4a,9,9a-hexahydro-1 H-indeno[2,1-b]pyridin-6-yl)- benzenesulfonamide; the 2nd product, 4-isopropyl-N-((4aR,9aR)-1-propyl-2,3,4,4a, 9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl)-benzenesulfonamide, was obtained as a colorless oil (8.5 mg, 2%).4-lsopropyl-N-((4aS,9aS)-1-propyl-2,3>4,4a,9I9a-hexahydro-1 H-indeno[2,1- b]pyridin-6-yl)-benzenesulfonamide:MS (ESI) m/z: 413.1 [M+H]+M/45291 EPO <DP n=101/>1H-NMR (DMSO): delta [ppm] 7.69 (d, 2H), 7.42 (d, 2H), 7.14 (d, 1 H), 6.94 (m, 2H), 3.60 (d, 1H), 3.30 (m, 1 H), 3.15 (m, 2H), 2.90 (m, 4H), 2.65 (m, 4H), 2.22 (m, 1H), 1.91 (m, 1H), 1.70 (m, 2H), 1.22 (d, 6H), 0.88 (t, 3H);4-lsopropyl-N-((4aR,9aR)-1-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1- b]pyridin-6-yl)-benzenesuIfonamide: MS (ESI) m/z: 413.1 [M+H]+ 1H-NMR (DMSO): delta [ppm] 7.68 (d, 2H), 7.41 (d, 2H), 7.14 (m, 2H), 6.94 (m, 1H), 3.61 (d, 1 H), 3.22 (m, 2H), 3.13 (m, 1 H), 2.92 (m, 5H), 2.31 (m, 2H), 1.95 (m, 2H), 1.74 (m, 2H), 1.40 (m, 2H), 1.19 (d, 6H), 0.93 (t, 3H).EXAMPLE 5 (reference example) N-((R)-2-Amino-indan-5-yl)-4-(2,2-difluoro-cyclopropyl)-benzenesulfonamide Following the standard sulphonamide coupling procedure analogous to that de¬ scribed above and TFA deprotection of the BOC-group as described above the ti¬ tle compound was prepared. Yield for the two steps: 65%. MS (ESI) m/z: 365.1 [M+H]+ 1H-NMR (DMSO): delta [ppm] 10.24 (s, 1H), 8.00 (br s, 2H), 7.71 (d, 2H), 7.48 (d, 2H), 7.12 (d, 1H), 7.02 (s, 1H), 6.96 (d, 1H), 3.96 (m, 1H), 3.14 (m, 3H), 2.83 (m,2H), 2.01 (m, 2H).

Reference： [1]Patent: WO2006/40177,2006,A1 .Location in patent: Page/Page column 99-100

43
[ 54997-90-9 ]
[ 869059-98-3 ]
1-[[4-(1-methylethyl)phenyl]sulfonyl]-2,3-dihydro-N-(2-phenylethyl)-2S-1H-indole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With cesium fluoride; In acetonitrile; at 20℃; for 20h;	96 mg (0.38 mmol) of morpholine resin (morpholinomethyl PS-HL 2% resin DVB Novabiochem) are conditioned in 3 ml of dichloromethane. Following elimination of the solvent, 1 ml of acetonitrile, 52.4 mg (0.24 mmol) of 4(1-methylethyl)benzenesulfonyl chloride, 50 mg (0.187 mmol) of the compound obtained according to preparation VI, and then 3 mg (0.19 mmol) of cesium fluoride are added in succession. The reaction medium is then agitated at ambient temperature. After 20 hours of agitation, the resin is filtered and the filtrate is recovered in 3 ml of dichloromethane and treated with 92 mg (0.24 mmol) of polyamine resin (polyamine resin HL Novabiochem). After 20 hours of agitation, the resin is filtered and the filtrate is recovered in 3 ml of dichloromethane and treated with 0.37 mmol of IR120 Amberlite resin. After 20 hours of agitation, the resin is filtered and the filtrate is concentrated and then dried under reduced pressure. In this way the expected product is obtained in the form of a white solid (yield=45%). NMR 1H (DMSO, 300 MHz) delta: 8.17 (t, 1H, NHCO), 7.68 (d, 2H, Harom.), 7.47-7.40 (m, 3H, Harom.), 7.27-7.17 (m, 6H, Harom.), 7.10 (d, 1H, Harom.), 7.01 (t, 1H, Harom.), 4.71 (dd, 1H, NCHCO), 3.34 (m, 2H, CH2NCO), 3.02-2.91 (m, 2H, CH2CHCO, CH(CH3)2), 2.82 (dd, 1H, CH2CHCO), 2.73 (t, 2H, CH2Ph), 1.16 (d, 6H, CH(CH3)2). MS (ESI+) m/z 449 (MH+).

Reference： [1]Patent: US2007/99960,2007,A1 .Location in patent: Page/Page column 13

44
[ 54997-90-9 ]
[ 1063993-43-0 ]
[ 1063993-36-1 ]

Yield	Reaction Conditions	Operation in experiment
33%		3-(1 H-lndol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester (135 mg, 0.5 mmol) was dissolved in DMF (10 ml) and cooled to 00C. Sodium hydride (35.7 mg, 0.74 mmol) was added, and the reaction mixture was stirred for 1 hour at 00C. 4-lsopropyl-benzene- sulfonyl chloride (98 mul, 0.55 mmol) was added slowly to the reaction mixture. Stirring was continued for 10 minutes. Cold water (100 ml) was added to the reaction mixture, and it was extracted twice with diethyl ether (80 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent was evaporated under reduced pressure to give a crystalline solid (75 mg, 33 %). ESI-MS [m/z]: 355.15 [M-(Boc)+H]+.

Reference： [1]Patent: WO2008/116833,2008,A1 .Location in patent: Page/Page column 49

45
[ 54997-90-9 ]
[ 1022953-85-0 ]
C₂₅H₃₀N₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		tert-Butyl l,3,4,8-tetrahydro-2H-[l,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 18, 14 mg, 0.050 mmol), NaH (60% in mineral oil, 6.4 mg, 0.10 mmol) and dry DMF (0.2 mL) were shaken at room temperature for 10 minutes. 4- Isopropylbenzenesulfonyl chloride (22 mg, 0.10 mmol, in 0.15 mL of dry DMF) was added to the solution. The reaction mixture was shaken at room temperature for another 20 minutes and a mixture of MeOH/1 M HCl (3 : 1, 1 mL) was added. The reaction mixture was stirred overnight and evaporated. The residue was dissolved in 1 M NH3 in MeOH (1 mL, 1 mmol) and MeOH (1 mL). The crude product was purified by preparative HPLC (XTerra C 18, 50 mM NH4HCO3 pH 10 - CH3CN) to give the title compound as an off-white solid (2.9 mg). MS m/z 371 [M + H]+.

Reference： [1]Patent: WO2008/54288,2008,A1 .Location in patent: Page/Page column 80

46
[ 54997-90-9 ]
5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-butanoic acid methyl ester [ No CAS ]
1-[[4-(1-methylethyl)phenyl]sulfonyl]-5-(trifluoromethyl)-1H-pyrrolo-[3,2-b]pyridine-2-butanoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		EXAMPLE 262 1-[[4-(1-Methylethyl)phenyl]sulfonyl]-5-(trifluoromethyl)-1H-pyrrolo-[3,2-b]pyridine-2-butanoic acid, methyl ester A solution of 0.263 g (0.92 mM) of the compound according to Preparation XLV in 10 ml of DMF is prepared and 73 mg (1.8 mM) of sodium hydride as a 60% suspension in oil are added at 0 C. The mixture is stirred for 15 minutes at 0 C., and 0.302 g (1.4 mM) of 4-(1-methylethyl)benzenesulfonamide chloride is then added. The reaction medium is stirred for 60 hours at room temperature and then poured into a mixture of crushed ice and ammonium chloride, and extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulfate and concentrated under reduced pressure. The expected compound is thus obtained in the form of a brown solid (yield=93%). m.p.=78 C.

Reference： [1]Patent: US2008/200495,2008,A1 .Location in patent: Page/Page column 33

47
[ 54997-90-9 ]
[ 883902-58-7 ]
[ 64-19-7 ]
4-isopropyl-N-(2-propyl-2,3,4,9-tetrahydro-1H-beta-carboline-7-yl)-benzenesulfonamide acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		2-Propyl-2,3,4,9-tetrahydro-1 H-beta-carbolin-7-ylamine (100 mg, 0.41 mmol) and 4- isopropyl-phenyl-sulfonyl chloride (91 mg, 0.41 mmol) were dissolved in tetrahydrofu- ran (15 ml). Triethylamine (0.17 ml, 1.24 mmol) was added and the reaction mixture stirred over night at room temperature. The solvent was evaporated under reduced pressure, the residue treated with H2O and extracted twice with ethyl acetate (50 ml). The organic layer was dried over magnesium sulfate, filtered, and the solvent evapo¬ rated under reduced pressure to give the crude product. The crude product was puri¬ fied via preparative HPLC (DeltaPak, 40 mm diameter) with acetonitrile/water/0.01% acetic acid as eluent to give the desired product (40 mg, 22 % yield). ESI-MS: 412.1 [M+H]+ 1H-NMR (DMSOd6, 400 MHz): delta [ppm] 10.6 (bs, 1 H), 9.8 (bs, 1 H), 7.6 (d, 2H), 7.4 (d, 2H), 7.2 (d, 1H), 7.1 (s, 1H), 6.7 (dd, 1H), 3.5 (bs, 2 H), 2.9 (sept, 6H), 2.7 (m, 2H), 2.6 (m, 2H), 2.5 (m, 2H), 1.9 (bs, 1 H), 1.5 (m, 2H), 1.2 (d, 6H), 0.9 (t, 3H). 13C-NMR (DMSOd6, 100 MHz): delta [ppm] 172.1 (s), 153.1 (s), 137.3 (s), 135.8 (s), 130.8 (S), 126.9 (d), 126.8 (d), 124.0 (s), 117.4 (d), 113.4 (d), 106.4 (s), 104.1 (d), 59.0 (t), 50.7 (t), 49.9 (t), 33.2 (d), 23.4 (q), 21.0 (t), 19.9 (t), 11.7 (q).

Reference： [1]Patent: WO2006/40180,2006,A1 .Location in patent: Page/Page column 113

48
[ 54997-90-9 ]
[ 859164-44-6 ]
1-(4-isopropylbenzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Sodium hydride (50 % suspension in mineral oil, 0.084 mmole) was taken in 3 mL dimethylformamide in a round bottomed flask under nitrogen atmosphere at room temperature. A solution of 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (0.065 mmole) dissolved in 3 mL of dimethylformamide at room temperature was added to the above mass and stirred for 45 min. A solution of 4-fluoro benzenesulfonyl chloride (0.091 mmole) in 2 ml dimethylformamide was added to the above reaction mass and the mass was further stirred for 2 hr at room temperature (25 oC) while monitoring the progress of the reaction by TLC. After completion of the reaction, the reaction mass was quenched on to water (25 mL) and extracted the product with ethyl acetate (2 x 25 mL). The combined organic layer was washed with brine solution (1 x 100 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography, using ethyl acetate and n-hexane in 8:2 ratio, to obtain the title compound 7h.