[ CAS No. 478264-00-5 ] {[proInfo.proName]}

Name: 478264-00-5|6-Methylpyridine-3-sulfonyl chloride|95%
Brand: Ambeed
SKU: A547422
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Quality Control of [ 478264-00-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 478264-00-5 ]

Product Details of [ 478264-00-5 ]

CAS No. :	478264-00-5	MDL No. :	MFCD11868981
Formula :	C₆H₆ClNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TWKVSHBWJUMVDX-UHFFFAOYSA-N
M.W :	191.64	Pubchem ID :	22398714
Synonyms :

Calculated chemistry of [ 478264-00-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.29
TPSA :	55.41 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.5
Log Po/w (XLOGP3) :	1.27
Log Po/w (WLOGP) :	2.4
Log Po/w (MLOGP) :	0.24
Log Po/w (SILICOS-IT) :	1.3
Consensus Log Po/w :	1.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.31 mg/ml ; 0.00683 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	1.78 mg/ml ; 0.00927 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.212 mg/ml ; 0.00111 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 478264-00-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501	UN#:	1759
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 478264-00-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 478264-00-5 ]

[ 478264-00-5 ] Synthesis Path-Downstream 1~24

1
1-(3-trifluoromethyl-5-cyanophenyl)piperazine [ No CAS ]
2-(trans-4-aminocyclohexyl)ethanol [ No CAS ]
[ 478264-00-5 ]
C₂₆H₃₂F₃N₅O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction.;

Reference： [1]Agai-Csongor, Eva; Nogradi, Katalin; Galambos, Janos; Vago, Istvan; Bielik, Attila; Magdo, Ildiko; Ignacz-Szendrei, Gyoergyi; Keseru, Gyoergy Miklos; Greiner, Istvan; Laszlovszky, Istvan; Bela Kiss, Eva Schmidt; Judit Laszy, Katalin Saghy; Gyertyan, Istvan; Zajer-Balazs, Maria; Gemesi, Larisza; Domany, Gyoergy [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5340 - 5344]

2
[ 478264-00-5 ]
[ 478263-99-9 ]
[ 478263-70-6 ]

Yield	Reaction Conditions	Operation in experiment
		69.c 5-Methoxy-2-(6-methylpyridine-3-sulfonylamino)-N-(1-phenylpropyl)-benzamide c) 67 mg of 5-methoxy-2-(6-methylpyridine-3-sulfonylamino)-N-(1-phenylpropyl)-benzamide were obtained as a white solid by general method 7 from 445 mg of (S)-2-amino-5-methoxy-N-(1-phenylpropyl)-benzamide and 300 mg of 6-methyl pyridine-3-sulfonyl chloride. MS (ES): 440 (M+H)+

Reference： [1]Current Patent Assignee: SANOFI - US2003/114499, 2003, A1

Yield	Reaction Conditions	Operation in experiment
14%

4
5-Amino-2-methylpyridine [ No CAS ]
[ 478264-00-5 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: 5-Amino-2-methylpyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: With hydrogenchloride; sodium hydrogensulfite; copper(II) sulfate In water at 0 - 20℃; for 0.5h;	186 Reference Example 186 6-methylpyridin-3-ylsulfonyl chloride; To a mixture of 6-methylpyridine-3-amine (449 mg) and concentrated hydrochloric acid (5 mL) was added a solution of sodium nitrite (857 mg) in water (2 mL) at 0° C., and the mixture was stirred at the same temperature for 10 min. To the mixture was added a solution of concentrated hydrochloric acid (2.5 mL), copper sulfate (69 mg) and sodium hydrogen sulfite (5.08 g) in water (8 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1) to give the title compound as a pale-yellow solid (yield 0.12 g, 15%). 1H-NMR (CDCl3)δ: 2.73 (3H, s), 7.40-7.43 (1H, m), 8.16-8.20 (1H, m), 9.11-9.12 (1H, m).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2007/60623, 2007, A1 Location in patent: Page/Page column 50

5
[ 478264-00-5 ]
[ 928325-23-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: tert-butyl N-[(5-bromo-1H-pyrrol-3-yl)methyl]-N-methylcarbamate With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 6-methylpyridine-3-sulfonyl chloride With 15-crown-5 In tetrahydrofuran at 0 - 20℃; for 0.5h;	187 Reference Example 187 tert-butyl({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate; To a solution of tert-butyl[(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (207 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 31 mg) at 0° C., and the mixture was stirred at the same temperature for 10 min. A solution (3 mL) of 15-crown-5 (0.16 mL) and 6-methylpyridin-3-ylsulfonyl chloride (117 mg) in tetrahydrofuran was added at the same temperature. After stirring at room temperature for 30 min, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a brown oil (yield 213 mg, 79%). 1H-NMR (CDCl3) δ: 1.47 (9H, s), 2.66 (3H, s), 2.79 (3H, s), 4.17 (2H, brs), 6.26 (1H, brs), 7.26-7.33 (2H, m), 8.03-8.07 (1H, m), 9.01-9.02 (1H, m).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2007/60623, 2007, A1 Location in patent: Page/Page column 50-51

6
[ 478264-00-5 ]
[ 1055306-34-7 ]
[ 1055306-35-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 5-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With 15-crown-5 In tetrahydrofuran for 0.0833333h; Stage #3: 6-methylpyridine-3-sulfonyl chloride In tetrahydrofuran at 20℃; for 1h;	15 Reference Example 15; 5- (2-chloropyridin-3-yl ) -1- [ ( 6-methylpyridin-3-yl ) sulfonyl ] - lH-pyrrole-3-carbaldehyde; To a solution of 5- (2-chloropyridin-3-yl) -lH-pyrrole-3- carbaldehyde (207 mg) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 100 mg) at room temperature and the mixture was stirred for 10 min. 15-Crown-5 (552 mg) was added dropwise, and the mixture was stirred for 5 min. 6- Methylpyridine-3-sulfonyl chloride (250 mg) was added, and the mixture was further stirred for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The, extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→l :4) to give the title compound as a colorless oil (yield 90 mg, 25%) .1H-NMR (CDCl3) δ: 2.65(3H, s), 6.73 (IH, d, J=I .5Hz) , 7.23 (IH, d, J=8.3Hz) , 7.37 (lH,dd, J=7.6Hz, 4.5Hz) , 7.53(lH,dd, J=8.3Hz, 2.3Hz) , 7.75 (lH,dd, J=I .6Hz, 1.9Hz) , 8.14(lH,d, J=I.9Hz) , 8.49 (IH, d, J=I .9Hz) , 8.51 (IH, d, J=I .9Hz) , 9.92{lH,s) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/108380, 2008, A2 Location in patent: Page/Page column 77-78

7
[ 478264-00-5 ]
[ 1138034-14-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 6-methylpyridine-3-sulfonyl chloride With sodium hydrogencarbonate; sodium sulfite In water at 80℃; for 1h; Stage #2: In ethanol at 80℃; for 0.5h;	70 Sodium 6-methylpyridine-3-sulfinate Reference Example 70 Sodium 6-methylpyridine-3-sulfinate Anhydrous sodium sulfite (2.65 g) and sodium hydrogen carbonate (1.77 g) were suspended in water (10 mL), 6-methylpyridine-3-sulfonyl chloride (2.0 g) was added, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, ethanol (50 mL) was added to the obtained residue, and the mixture was stirred at 80° C. for 30 min. The reaction mixture was filtered to remove the insoluble material, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the insoluble solid was collected by filtration to give the title compound as a pale-yellow powder (1.4 g, yield 75%). 1H-NMR (DMSO-d6) δ: 2.44 (3H, s), 7.18 (1H, d, J=8.0 Hz), 7.68 (1H, dd, J=8.0, 1.9 Hz), 8.46 (1H, s).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2009/156642, 2009, A1 Location in patent: Page/Page column 47

8
[ 907202-06-6 ]
[ 478264-00-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 5-(benzylthio)-2-methylpyridine With N-chloro-succinimide; water; acetic acid at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In water	67 6-methylpyridine-3-sulfonyl chloride Reference Example 67 6-methylpyridine-3-sulfonyl chloride 5-(Benzylsulfanyl)-2-methylpyridine (11.7 g) was dissolved in a mixed solvent of acetic acid (120 mL)-water (40 mL), N-chlorosuccinimide (29.0 g) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1) to give the title compound as a pale-brown solid (7.87 g, yield 76%). 1H-NMR (CDCl3) δ: 2.73 (3H, s), 7.43 (1H, d, J=8.3 Hz), 8.19 (1H, dd, J=8.3, 2.7 Hz), 9.12 (1H, d, J=2.7 Hz).
45%	With N-chloro-succinimide In water; acetic acid at 20℃; for 2h;	19 Synthesis of 6-methylpyridine-3-sulfonyl chloride (108): To a stirred solution of compound 107 (250 mg, 1.16 mmol) in AcOH/ H20 (3 : 1, 16 mL) was added N- chlorosuccinimide (1.38 g, 11.60 mmol) at RT; stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo, the residue was neutralized with aqueous saturated NaHC03 solution (30 mL) and extracted with CH2C12 (2 x 40 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 108 (100 mg, 45%) as yellow oil. TLC: 20% EtOAc/ hexanes (Rf. 0.3); 1H-NMR (CDC13, 400 MHz): δ 9.12 (s, 1 H), 8.18 (d, J= 8.0 Hz, 1H), 7.41 (d, J= 8.4 Hz, 1H), 2.72 (s, 3H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2009/156642, 2009, A1 Location in patent: Page/Page column 46
[2]Current Patent Assignee: ASSEMBLY BIOSCIENCES, INC. - WO2016/168619, 2016, A1 Location in patent: Paragraph 00209

9
[ 478264-00-5 ]
5-amino-2-(trifluoromethyl)pyridine-4-ol [ No CAS ]
N-[4-hydroxy-6-(trifluoromethyl)pyridin-3-yl]-6-methylpyridine-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With pyridine at 80℃; for 1h;	132 N-[4-hydroxy-6-(trifluoromethyl)pyridiii-3-yl]-6-methylpyridine-3-sulfonamide To a stirred solution of 5-amino-2-(trifiuoromethyl)pyridin-4-ol (150 mg at 50% purity, 0.421 mrnol ) in pyridine at 80°C was added 6-methylpyridine-3-sulfonyl chloride (prepared according to a method described in WO 2007/023186 Al), 55 mg, 0.29 mmol). The mixture was stirred for 1 hr at this temperature then the pyridine was evaporated. The residue was purified by low pH automated preparative HPLC to afford the title compound as a white solid (10 mg, 7%).

Reference： [1]Current Patent Assignee: ACTIVE BIOTECH AB - WO2014/184234, 2014, A1 Location in patent: Page/Page column 164

10
[ 4808-69-9 ]
[ 478264-00-5 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 13093 - 13104

11
[ 3430-13-5 ]
[ 478264-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; triethylamine / toluene / 16 h / 100 °C / Inert atmosphere 2: N-chloro-succinimide / water; acetic acid / 2 h / 20 °C

Reference： [1]Current Patent Assignee: ASSEMBLY BIOSCIENCES, INC. - WO2016/168619, 2016, A1

12
[ 478264-00-5 ]
[ 1055306-88-1 ]
[ 1210868-09-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 15-crown-5; sodium hydride In tetrahydrofuran at 20℃; for 1h;	S.39. tert-Butyl [4-fluoro-5-(2-fluoropyridin-3-yl)-1-(thiophen-2-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (19a) General procedure: To a suspension of sodium hydride (60% in oil, 37 mg, 0.93 mmol) in THF (2 mL) were added dropwise a solution of compound 18 (200 mg, 0.62 mmol) in THF (1 mL), then 15-crown-5 (205 mg, 0.93 mmol) and 2-thiophenesulfonyl chloride (136 mg, 0.74 mmol) at room temperature. After stirred for 1 h, the reaction mixture was diluted with H2O, and extracted with EtOAc. The extract was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane/EtOAc = 6/1-3/2) to obtain compound 19a (276 mg, 95%) as a colorless oil: 1H-NMR (CDCl3) d 1.48 (9H, s), 2.87 (3H, s), 4.27 (2H, brs), 7.19-7.33 (4H, m), 7.63 (1H, dd, J = 5.0 Hz, 1.0 Hz), 7.84 (1H, ddd, J = 9.2 Hz, 7.4 Hz, 1.9 Hz), 8.25-8.32 (1H, m).

Reference： [1]Nishida, Haruyuki; Fujimori, Ikuo; Arikawa, Yasuyoshi; Hirase, Keizo; Ono, Koji; Nakai, Kazuo; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3447 - 3460]

13
[ 478264-00-5 ]
(R)-1-(4-cyclopropoxybenzyl)pyrrolidin-3-amine hydrochloride [ No CAS ]
C₂₀H₂₅N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dichloromethane; water Inert atmosphere;

Reference： [1]Hurley, Katherine A.; Santos, Thiago M. A.; Fensterwald, Molly R.; Rajendran, Madhusudan; Moore, Jared T.; Balmond, Edward I.; Blahnik, Brice J.; Faulkner, Katherine C.; Foss, Marie H.; Heinrich, Victoria A.; Lammers, Matthew G.; Moore, Lucas C.; Reynolds, Gregory D.; Shearn-Nance, Galen P.; Stearns, Brian A.; Yao, Zi W.; Shaw, Jared T.; Weibel, Douglas B. [MedChemComm, 2017, vol. 8, # 5, p. 942 - 951]

14
[ 478264-00-5 ]
(R)-1-([1,1′-biphenyl]-4-ylmethyl)pyrrolidin-3-amine hydrochloride [ No CAS ]
C₂₃H₂₅N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dichloromethane; water Inert atmosphere;

15
[ 478264-00-5 ]
C₁₄H₂₂N₂O [ No CAS ]
C₂₀H₂₇N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dichloromethane; water Inert atmosphere;

16
[ 123-75-1 ]
[ 478264-00-5 ]
C₁₀H₁₄N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine

Reference： [1]Current Patent Assignee: UNIVERSITY OF NANTES; UNIVERSITY OF ORLEANS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - WO2020/94754, 2020, A1 Location in patent: Page/Page column 21

17
[ 478264-00-5 ]
pyrrolidine-2-carbonitrile [ No CAS ]
C₁₁H₁₃N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine

Reference： [1]Current Patent Assignee: UNIVERSITY OF NANTES; UNIVERSITY OF ORLEANS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - WO2020/94754, 2020, A1 Location in patent: Page/Page column 21

18
[ 478264-00-5 ]
(2S)-pyrrolidine-2-carbonitrile hydrochloride [ No CAS ]
(S)-1-((6-methylpyridin-3-yl)sulfonyl)pyrrolidine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: (2S)-pyrrolidine-2-carbonitrile hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 6-methylpyridine-3-sulfonyl chloride In dichloromethane at 20℃; for 16h;	13 Example 13: Compound 3ec: preparation of (S)-1-((6-methylpyridin-3- yl)sulfonyl)pyrrolidine-2- carbonitrile To a mixture of (S)-pyrrolidine-2-carbonitrile hydrochloride (32.5 mg, 0.25 mmol, 1 .1 eq) in methylene chloride (10 ml_) was added triethylamine (45 mg, 0.06 ml_, 0.45 mmol, 2 eq). The mixture was stirred during 15 min, 6-methylpyridine-3- sulfonyl chloride (42.7 mg, 0.22 mmol, 1 eq) was added and the stirring was continued for additional 16 h. The mixture was then hydrolyzed with an aqueous solution of HCI (2M) and extracted with methylene chloride. The organic layer was washed with water, dried over MgS04, filtrated and evaporated under vacuum. The crude product was purified by column chromatography (Si02, petroleum ether/EtOAc: 6/4) to afford the product as a white solid in 70% yield. (0257) mp: 120°C (0258) RMN 1H NMR (400 MHz, CDCI3): d 8.98 (d, 1 H, 2.1 Hz, H2); 8.08 (dd, 2H, 8.4 Hz and 2.1 Hz, H4); 7.35 (d, 1 H, 8.4 Hz, H5); 4.66 (dd, 1 H, 7.1 Hz and 3.2 Hz, H2); 3.48 (mt, 1 H, H5·,a); 3.36 (m, 1 H, H5·,b); 2.28-2.19 (m, 2H, H3. a and H3. p); 2.15-2.06 (m, 2H, H4',a and H4 b). (0259) RMN 13C NMR (100 MHz, CDCI3): 164.2 (C6); 147.7 (C2); 135.4 (C4); 131 .6 (C3); 123.5 (C5); 1 17.6 (CN); 48.6 (C2); 47.3 (C5); 31 .9 (C3); 27.8 (CH3); 24.7 (C4). (0260) MS: ESI+: [M+H]+ = 252.1 ; [M+Na]+ = 274.1 .HRMS (ESI+) calculated for Cn H13N3Na02S [M+Na]+ m/z = 274.0626 found 274.0631 . (0262) [a]D20°c: -93.3 (0.5 g/100 ml_) in MeOH. (0263) IR ATR: v (cm 1) 3065.82-2995.28 (=C-H); 2939.80-2852.41 (-C-H); 2245.49 (CN); 1341 .03 (S02, as); 1 162.68 (S02,s).

Reference： [1]Current Patent Assignee: UNIVERSITY OF NANTES; UNIVERSITY OF ORLEANS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - WO2020/94754, 2020, A1 Location in patent: Page/Page column 21; 34

19
[ 478264-00-5 ]
3-amino-4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)benzamide [ No CAS ]
4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)-3-((6-methylpyridine)-3-sulfonamido)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; 4-dimethylaminopyridine In dichloromethane	19 Example 19: 4-methyl-N-[(1-methyl-1H-pyrazol-4-yl)methyl]-3-(6-methylpyridine-3-sulfonamido)benzamide Add 3-amino-4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)benzamide (0.073g, 0.3mmol),A reaction mixture of 6-methylpyridine-3-sulfonyl chloride (0.069 g, 0.36 mmol), DMAP (0.007 g, 0.06 mmol) and pyridine (0.036 g, 0.45 mmol) in DCM (5 mL) was stirred overnight. Water (25 mL) was added, and the resulting mixture was extracted with DCM (20 mL×3). The combined organic layer was washed with water (50 mL×2) and brine (50 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (silica gel, EtOAc/MeOH=10:1) to obtain the product as a white solid (88 mg, yield 73%).
73%	With pyridine; 4-dimethylaminopyridine In dichloromethane	19 Example 19: 4-Methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)-3-((6-methylpyridine)-3-sulfonamido)benzamide 3-Amino-4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)benzamide (0.073 g, 0.3 mmol),A reaction mixture of 6-methylpyridine-3-sulfonyl chloride (0.069 g, 0.36 mmol), DMAP (0.007 g, 0.06 mmol) and pyridine (0.036 g, 0.45 mmol) in DCM (5 mL) was stirred overnight. Water (25 mL) was added and the resulting mixture was extracted with DCM (20 mL x 3). The combined organic layers were washed with water (50 mL×2) and brine (50 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by preparative thin layer chromatography (silica gel, EtOAc/MeOH = 10:1) to give the product as a white solid (88 mg, 73% yield).

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN111285806, 2020, A Location in patent: Paragraph 0306-0310
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - WO2021/248256, 2021, A1 Location in patent: Page/Page column 32-33

20
[ 478264-00-5 ]
tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1H-pyrrol-3-yl)methyl)(methyl)carbamate [ No CAS ]
tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrol-3-yl) methyl)(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1H-pyrrol-3-yl)methyl)(methyl)carbamate With benzo-15-crown-5; sodium hydride In tetrahydrofuran at 50℃; for 0.166667h; Stage #2: 6-methylpyridine-3-sulfonyl chloride In tetrahydrofuran at 20℃; for 0.5h;	4.1 (1) step tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrol-3-yl) methyl) (methyl) carbamate Synthesis tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1H-pyrrol-3-yl)methyl)(methyl)carbamate (intermediate 2, 100.0 mg, 0.3 mmol), NaH (24.0 mg , 0.6 mmol) and 15-crown-5-ether (0.9 mL, 0.5 mmol) were dissolved in anhydrous THF (1.5 mL) and stirred at 50° C. for 10 minutes. 6-methylpyridine-3-sulfonyl chloride (86.0 mg, 0.5 mmol) was added and stirred at room temperature for 30 minutes. After adding distilled water to the reaction solution, it was washed with brine and extracted with EA. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to tert-butyl ((5-(2-fluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl) )sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate was obtained as a pale yellow oil. (60.9 mg, 42%)

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - WO2021/256861, 2021, A1 Location in patent: Paragraph 296-299

21
[ 478264-00-5 ]
methyl 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylate [ No CAS ]
methyl 5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: methyl 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylate With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.833333h; Stage #2: 6-methylpyridine-3-sulfonyl chloride In N,N-dimethyl-formamide at 50℃; for 16h;	3.1 (1) Step of methyl 5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrole-3-carboxylate synthesis Methyl 5-(2,4-difluorophenyl)-4-methoxy-1H-pyrrole-3-carboxylate (intermediate 3, 1.0 eq., 534 mg, 2.0 mmol) with NaH (1.5 eq., 120 mg , 3.0 mmol) was dissolved in anhydrous DMF (10.0 mL) and stirred at 50° C. for 50 minutes. 6-methylpyridine-3-sulfonyl chloride (1.5 eq., 575 mg, 3.0 mmol) was added and stirred at 50° C. for 16 hours. After adding distilled water to the reaction solution, it was washed with brine and extracted with EA. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to methyl 5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl) Sulfonyl)-1H-pyrrole-3-carboxylate was obtained. (614 mg, 73%)

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - WO2021/256861, 2021, A1 Location in patent: Paragraph 286-289

22
[ 478264-00-5 ]
1-(5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 50 °C 1.2: 16 h / 50 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C 4.1: tetrahydrofuran; methanol / 0.5 h / 20 °C 4.2: 0.17 h

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - WO2021/256861, 2021, A1

23
[ 478264-00-5 ]
(5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrol-3-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 50 °C 1.2: 16 h / 50 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - WO2021/256861, 2021, A1

24
[ 478264-00-5 ]
5-(2,4-difluorophenyl)-4-methoxy-1-((6-methylpyridin-3-yl)sulfonyl)-1H-pyrrole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 50 °C 1.2: 16 h / 50 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - WO2021/256861, 2021, A1

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Synthesis of an Alkyl Sulfonate • The Conversion of Carboxylic Acids into Acyl Halides

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A1062058[ 1210868-11-3 ]

6-Methylpyridine-3-sulfonyl chloride hydrochloride

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H316	Causes mild skin irritation
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Code	Phrase
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 478264-00-5 ] Synthesis Path-Downstream 1~24

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Similar Product of [ 478264-00-5 ]

Related Functional Groups of [ 478264-00-5 ]

Sulfonyl Chlorides

Chlorides

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Pyridines

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