[ CAS No. 1828-66-6 ] {[proInfo.proName]}

Name: 1828-66-6|Morpholine-4-sulfonyl chloride|95%
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SKU: A155311
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Quality Control of [ 1828-66-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1828-66-6 ]

Product Details of [ 1828-66-6 ]

CAS No. :	1828-66-6	MDL No. :	MFCD03249981
Formula :	C₄H₈ClNO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KXIBCCFSAMRWIC-UHFFFAOYSA-N
M.W :	185.63	Pubchem ID :	12798265
Synonyms :

Calculated chemistry of [ 1828-66-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.88
TPSA :	54.99 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	-0.08
Log Po/w (WLOGP) :	0.5
Log Po/w (MLOGP) :	-0.52
Log Po/w (SILICOS-IT) :	0.06
Consensus Log Po/w :	0.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.87
Solubility :	24.8 mg/ml ; 0.134 mol/l
Class :	Very soluble
Log S (Ali) :	-0.62
Solubility :	44.2 mg/ml ; 0.238 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.61
Solubility :	45.8 mg/ml ; 0.247 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.46

Safety of [ 1828-66-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1828-66-6 ]

* 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 [ 1828-66-6 ]
Downstream synthetic route of [ 1828-66-6 ]

[ 1828-66-6 ] Synthesis Path-Upstream 1~6

1
[ 110-91-8 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuryl dichloride In acetonitrile for 24 h; Heating / reflux	Morpholine (0.436 mL, 5 mmol) was added slowly and with caution to a mixture of sulfuryl chloride (1.205 mL, 15 mmol) in 5 mL acetonitrile. Heated to reflux and stirred for 24 hours. After starting material consumed, solution concentrated to oil, azeotroped with toluene (2x), concentrated to give crude product 126 stored as a 2M solution in dichloromethane (0.999 g, 5 mmol, 100percent. ) ¹H NMR (CD3SOCD3) No. 3.80 (br s, 4H), 3.28 (br s, 4H.) MS: 186 (M+1)
60%	With hydrogenchloride; sodium hypochlorite; sulfur dioxide; chlorine In dichloromethane; water	Preparation Example 23 Preparation of N-morpholinesulfonyl chloride A mixture of 16 g of conc. hydrochloric acid, 16 g of water and 14.2 g of morpholine was cooled to 5° C. and 80 ml of dichloromethane was added thereto. 315 g of 4percent NaOCl was added at 5° C. over 60 minutes and the mixture was stirred at room temperature for 50 minutes. The dichloromethane layer was separated, dried over MgSO₄ and cooled to -70° C. 24 g of SO₂ and 100 ml of dichloromethane were further added thereto. 3 ml of chlorine gas was condensed into the resulting mixture and the mixture was stirred for 24 hours, while warmed gradually to room temperature. The mixture was washed with 0.25M phosphate buffer, pH 7.0 until the washings are neutral. The dichloromethane layer was dried over anhydrous MgSO₄ and distilled under a reduced pressure to give the title compound (yield: 60percent). ¹ H NMR(CDCl₃) δ1.2-1.7(5H, m, d), 2.4-3.2(12H, m), 3.7 (4H, br), 3.9(2H, m), 4.7(1H, m), 6.8(1H, br), 6.9(1H, br), 7.05-7.4(10H, m), 7.5(1H, d), 7.7-7.8(1H, dd), 8.3-8.5(1H, dd) Mass(FAB, m/e) 602(M+1)
60%	With hydrogenchloride; sodium hypochlorite; sulfur dioxide; chlorine In dichloromethane; water	Preparation Example 23: Preparation of N-morpholinesulfonyl chloride A mixture of 16g of conc. hydrochloric acid, 16g of water and 14.2g of morpholine was cooled to 5°C and 80ml of dichloromethane was added thereto. 315g of 4percent NaOCl was added at 5°C over 60 minutes and the mixture was stirred at room temperature for 50 minutes. The dichloromethane layer was separated, dried over MgSO₄ and cooled to -70°C. 24g of SO₂ and 100ml of dichloromethane were further added thereto. 3ml of chlorine gas was condensed into the resulting mixture and the mixture was stirred for 24 hours, while warmed gradually to room temperature. The mixture was washed with 0.25M phosphate buffer, pH 7.0 until the washings are neutral. The dichloromethane layer was dried over anhydrous MgSO₄ and distilled under a reduced pressure to give the title compound (yield: 60percent). ¹H NMR(CDCl₃) δ 1.2-1.7(5H, m, d), 2.4-3.2(12H, m), 3.7 (4H, br), 3.9(2H, m), 4.7(1H, m), 6.8(1H, br), 6.9(1H, br), 7.05-7.4(10H, m), 7.5(1H, d), 7.7-7.8(1H, dd), 8.3-8.5(1H, dd) Mass(FAB, m/e) 602(M+1)

40%	With sulfuryl dichloride In acetonitrile at 0 - 85℃;	8.4 ml (96.4 mmol) morpholine in 12 ml acetonitrile were metered into a solution of 4.0 ml (49.3 mmol) sulphuryl chloride in 12 ml acetonitrile while cooling with an ice bath and the mixture was stirred overnight at 85° C. Then the reaction solution was evaporated down i. vac., the residue was combined with diethyl ether, the precipitate was filtered off and the filtrate was distilled under a pressure of 1 mbar and a head temperature of 95-98° C. Yield 3.7 g (40percent) colourless oil 13-a.
0.23%	With sulfuryl dichloride; trimethylamine In dichloromethane for 2 h; Cooling with ice	10.0 mL of dichloromethane (CH₂Cl₂) was added to a 50-mL round-bottomed flask, which was then cooled down in an ice bath (low-temperature bath). After 0.300 mL of sulfuryl chloride (SO₂Cl₂) was added thereto, a solution of 213 mg of morpholine dissolved in 3.0 mL of dichloromethane (CH₂Cl₂) was slowly added while cooling in the ice bath (low-temperature bath). The reaction mixture was treated with 520 mg of trimethylamine and then stirred for about 2 hours. The resulting reaction product was dissolved with 20.0 mL of chloroform and then washed with 20.0 mL of ice water. The chloroform phase was separated, dried with magnesium sulfate (MgSO₄), and then filtered. The resulting filtrate was distilled under reduced pressure. As a result, 160 mg of morpholine-4-sulfonyl chloride was obtained with a yield of about 23.3percent. 70.0 mg of (R)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 5-mL round-bottomed flask and then dissolved with 1.00 mL of dichloromethane (CH₂Cl₂). After 0.0390 mL of morpholine-4-sulfonyl chloride was added thereto, the reaction mixture was treated with 0.0590 mL of N,N-diisopropylethylamine and then stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH₂Cl₂=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 47.0 mg of (R)-N-methyl-N-(1-(morpholinosulfonyl)pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 40.2percent. ¹H NMR (400 MHz, CDCl₃) δ10.06 (s, 1H), 8.39 (s, 1H), 7.11-7.10 (m, 1H), 6.62-6.61 (m, 1H), 5.84-5.76 (m, 1H), 3.78-3.77 (m, 4H), 3.70-3.64 (m, 2H), 3.45-3.29 (m, 9H), 2.36-2.17 (m, 2H). LRMS (ESI) calcd for (C₁₅H₂₂N₆O₃S + H⁺) 367.2, found 367.1.

Reference： [1] Patent: WO2005/117904, 2005, A2, . Location in patent: Page/Page column 463-464
[2] Patent: US5587388, 1996, A,
[3] Patent: EP601486, 1994, A1,
[4] Patent: US2006/223759, 2006, A1, . Location in patent: Page/Page column 218
[5] Justus Liebigs Annalen der Chemie, 1959, vol. 624, p. 25,29
[6] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 1935 - 1943
[7] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 3, p. 499 - 502
[8] Patent: US5643878, 1997, A,
[9] Patent: US6372778, 2002, B1, . Location in patent: Example 161
[10] Patent: US2004/6090, 2004, A1, . Location in patent: Page/Page column 34
[11] Patent: US5585397, 1996, A,
[12] Patent: US5783701, 1998, A,
[13] Patent: US2015/11535, 2015, A1, . Location in patent: Paragraph 0242-0243
[14] Patent: WO2015/3958, 2015, A1, . Location in patent: Page/Page column 44; 45
[15] Patent: WO2017/140778, 2017, A1, . Location in patent: Page/Page column 98
[16] Patent: EP3327021, 2018, A1, . Location in patent: Paragraph 0211-0215

2
[ 108085-16-1 ]
[ 1828-66-6 ]

Reference： [1] Patent: WO2006/77414, 2006, A1, . Location in patent: Page/Page column 170-171

3
[ 110-91-8 ]
[ 7791-25-5 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	for 24 h; Heating / reflux	Morpholine (0.436 mL, 5 mmol) was added slowly and with caution to a mixture of sulfuryl chloride (1.205 ml, 15 mmol) in 5 mL acetonitrile. Heated to reflux and stirred for 24 hours. After starting material consumed, solution concentrated to oil, azeotroped with toluene (2x), concentrated to give crude product 126 stored as a 2M solution in dichloromethane (0.999 g, 5 mmol, 100percent.) 1H NMR (CD3SOCD3) 8 3.80 (br s, 4H), 3.28 (br s, 4H. ) MS: 186 (M+1)

Reference： [1] Patent: WO2004/35576, 2004, A2, . Location in patent: Page 227

4
[ 10024-89-2 ]
[ 1828-66-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 23, p. 3820 - 3828
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 967 - 977

5
[ 23328-69-0 ]
[ 1828-66-6 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1959, vol. 624, p. 25,29

6
[ 15159-40-7 ]
[ 1828-66-6 ]

Reference： [1] Patent: DE946710, 1956, ,

[ 1828-66-6 ] Synthesis Path-Downstream 1~88

1
[ 110-91-8 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuryl dichloride; In acetonitrile; for 24h;Heating / reflux;	Morpholine (0.436 mL, 5 mmol) was added slowly and with caution to a mixture of sulfuryl chloride (1.205 mL, 15 mmol) in 5 mL acetonitrile. Heated to reflux and stirred for 24 hours. After starting material consumed, solution concentrated to oil, azeotroped with toluene (2x), concentrated to give crude product 126 stored as a 2M solution in dichloromethane (0.999 g, 5 mmol, 100%. ) ¹H NMR (CD3SOCD3) No. 3.80 (br s, 4H), 3.28 (br s, 4H.) MS: 186 (M+1)
60%	With hydrogenchloride; sodium hypochlorite; sulfur dioxide; chlorine; In dichloromethane; water;	Preparation Example 23 Preparation of N-morpholinesulfonyl chloride A mixture of 16 g of conc. hydrochloric acid, 16 g of water and 14.2 g of morpholine was cooled to 5 C. and 80 ml of dichloromethane was added thereto. 315 g of 4% NaOCl was added at 5 C. over 60 minutes and the mixture was stirred at room temperature for 50 minutes. The dichloromethane layer was separated, dried over MgSO4 and cooled to -70 C. 24 g of SO2 and 100 ml of dichloromethane were further added thereto. 3 ml of chlorine gas was condensed into the resulting mixture and the mixture was stirred for 24 hours, while warmed gradually to room temperature. The mixture was washed with 0.25M phosphate buffer, pH 7.0 until the washings are neutral. The dichloromethane layer was dried over anhydrous MgSO4 and distilled under a reduced pressure to give the title compound (yield: 60%). 1 H NMR(CDCl3) delta1.2-1.7(5H, m, d), 2.4-3.2(12H, m), 3.7 (4H, br), 3.9(2H, m), 4.7(1H, m), 6.8(1H, br), 6.9(1H, br), 7.05-7.4(10H, m), 7.5(1H, d), 7.7-7.8(1H, dd), 8.3-8.5(1H, dd) Mass(FAB, m/e) 602(M+1)
60%	With hydrogenchloride; sodium hypochlorite; sulfur dioxide; chlorine; In dichloromethane; water;	Preparation Example 23: Preparation of N-morpholinesulfonyl chloride A mixture of 16g of conc. hydrochloric acid, 16g of water and 14.2g of morpholine was cooled to 5C and 80ml of dichloromethane was added thereto. 315g of 4% NaOCl was added at 5C over 60 minutes and the mixture was stirred at room temperature for 50 minutes. The dichloromethane layer was separated, dried over MgSO4 and cooled to -70C. 24g of SO2 and 100ml of dichloromethane were further added thereto. 3ml of chlorine gas was condensed into the resulting mixture and the mixture was stirred for 24 hours, while warmed gradually to room temperature. The mixture was washed with 0.25M phosphate buffer, pH 7.0 until the washings are neutral. The dichloromethane layer was dried over anhydrous MgSO4 and distilled under a reduced pressure to give the title compound (yield: 60%). 1H NMR(CDCl3) delta 1.2-1.7(5H, m, d), 2.4-3.2(12H, m), 3.7 (4H, br), 3.9(2H, m), 4.7(1H, m), 6.8(1H, br), 6.9(1H, br), 7.05-7.4(10H, m), 7.5(1H, d), 7.7-7.8(1H, dd), 8.3-8.5(1H, dd) Mass(FAB, m/e) 602(M+1)

40%	With sulfuryl dichloride; In acetonitrile; at 0 - 85℃;	8.4 ml (96.4 mmol) morpholine in 12 ml acetonitrile were metered into a solution of 4.0 ml (49.3 mmol) sulphuryl chloride in 12 ml acetonitrile while cooling with an ice bath and the mixture was stirred overnight at 85 C. Then the reaction solution was evaporated down i. vac., the residue was combined with diethyl ether, the precipitate was filtered off and the filtrate was distilled under a pressure of 1 mbar and a head temperature of 95-98 C. Yield 3.7 g (40%) colourless oil 13-a.
	With sulfuryl dichloride;	36a N-Chlorosulfonylmorpholine With intensive cooling, 32.7 ml of sulfuryl chloride are added at approximately 0 C. to 23.5 ml of morpholine. The suspension is then carefully heated to 60 C., causing the onset of hydrogen chloride evolution. After 5 h at 60 C., the evolution of hydrogen chloride is complete. The cooled brown reaction mixture is poured onto ice, and the precipitating oil is extracted with ether, washed with water, 5% sodium hydrogen carbonate solution and water and dried with sodium sulfate. The organic phases are concentrated by evaporation and distilled at elevated temperature and reduced pressure (90 C.; 1 mbar) to yield the title compound: 1 H-NMR (200 MHz, DMSO-d6): 3.80 and 3.29 (2t, 5 Hz, per 4 H).
	With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20℃; for 1.25h;	The corresponding amine (10 mmol) was dissolved in anhydrous methylene chloride (20 mL) and treated with triethylamine (10 mmol). The mixture was placed in an ice bath and sulfonyl chloride (20 mmol) was added dropwise. The reaction mixture was stirred at 0 C. for 15 min., then at rt for 1 h. A saturated aqueous solution of sodium carbonate (50 mL) was used to quench the reaction, and the organics were extracted with methylene chloride (2×50 mL), dried over sodium sulfate and concentrated in vacuum. The sulfamoyl chloride was used without further purification. [0340] The following sulfamoyl chlorides were prepared following method B: Morpholinosulfamoyl choride.
	With sulfuryl dichloride; In acetonitrile;	A. 4-Morpholinesulfonyl Chloride A solution of 4.6 g of sulfuryl chloride in acetonitrile was treated dropwise with 996 mg of morpholine at ambient temperature under an atmosphere of nitrogen. After complete addition, the mixture was refluxed for 16 h, cooled to room temperature, and concentrated in vacuo to yield the title product as a red oil. TLC: Rf=0.65 CH2 Cl2. (1 H)-NMR (CDCl3) consistent with structure.
	With sulfuryl dichloride; In acetonitrile;	A. 4-Morpholinesulfonyl chloride A solution of 4.6 g of sulfuryl chloride in acetonitrile was treated dropwise with 996 mg of morpholine at ambient temperature under an atmosphere of nitrogen. After complete addition, the mixture was refluxed for 16 h, cooled to room temperature, and concentrated in vacuo to yield the title product as a red oil. TLC: Rf=0.65 CH2 Cl2. (1 H)-NMR (CDCl3) consistent with structure.
	With sulfuryl dichloride; In acetonitrile; for 24h;Reflux;	Morpholine (0.50 mL; 5.74 mmol) and sulfuryl chloride (1.50 mL; 18.50 mmol) in ACN (5 mL) are stirred at reflux for 24 hours. The solvent is removed and the residue is taken up in toluene, treated with activated charcoal and filtered off. The solvent is removed. [0243] C4H8ClNO3S
	With sulfuryl dichloride; In acetonitrile; for 24h;Reflux;	Stage 1: Morpholine (0.50 mL; 5.74 mmol) and sulfuryl chloride (1.50 mL; 18.50 mmol)in ACN (5 mL) are stirred at reflux for 24 hours. The solvent is removed and the residue is taken up in toluene, treated with activated charcoal and filtered off. The solvent is reremoved.C4H8ClNO3S
	With sulfuryl dichloride; In acetonitrile; for 24h;Reflux;	Morpholine (1 .98 mL, 22.9 mmol) was added slowly to a mixture of sulfuryl chloride (5.5 mL, 68.8 mmol) in acetonitrile (15 mL) at ambient temperature. The resulting reaction mixture was heated to reflux for 24 h. The solvent was removed in vacuo and the residue azeotroped twice with toluene to give morpholine-4-sulfonyl chloride as a light yellow oil (2.8 g, 67%). The crude product was used directly in the next step without further purification. 1 H NMR (400 MHz, DMSO-de): delta 3.79 (t, J = 4.0 Hz, 4H), 3.28 (t, J = 4.0 Hz, 4H).
Ca.23.3%	With sulfuryl dichloride; trimethylamine; In dichloromethane; for 2h;Cooling with ice;	10.0 mL of dichloromethane (CH2Cl2) was added to a 50-mL round-bottomed flask, which was then cooled down in an ice bath (low-temperature bath). After 0.300 mL of sulfuryl chloride (SO2Cl2) was added thereto, a solution of 213 mg of morpholine dissolved in 3.0 mL of dichloromethane (CH2Cl2) was slowly added while cooling in the ice bath (low-temperature bath). The reaction mixture was treated with 520 mg of trimethylamine and then stirred for about 2 hours. The resulting reaction product was dissolved with 20.0 mL of chloroform and then washed with 20.0 mL of ice water. The chloroform phase was separated, dried with magnesium sulfate (MgSO4), and then filtered. The resulting filtrate was distilled under reduced pressure. As a result, 160 mg of morpholine-4-sulfonyl chloride was obtained with a yield of about 23.3%. 70.0 mg of (R)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 5-mL round-bottomed flask and then dissolved with 1.00 mL of dichloromethane (CH2Cl2). After 0.0390 mL of morpholine-4-sulfonyl chloride was added thereto, the reaction mixture was treated with 0.0590 mL of N,N-diisopropylethylamine and then stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 47.0 mg of (R)-N-methyl-N-(1-(morpholinosulfonyl)pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 40.2%. 1H NMR (400 MHz, CDCl3) delta10.06 (s, 1H), 8.39 (s, 1H), 7.11-7.10 (m, 1H), 6.62-6.61 (m, 1H), 5.84-5.76 (m, 1H), 3.78-3.77 (m, 4H), 3.70-3.64 (m, 2H), 3.45-3.29 (m, 9H), 2.36-2.17 (m, 2H). LRMS (ESI) calcd for (C15H22N6O3S + H+) 367.2, found 367.1.

Reference： [1]Patent: WO2005/117904,2005,A2 .Location in patent: Page/Page column 463-464
[2]Patent: US5587388,1996,A
[3]Patent: EP601486,1994,A1
[4]Patent: US2006/223759,2006,A1 .Location in patent: Page/Page column 218
[5]Justus Liebigs Annalen der Chemie,1959,vol. 624,p. 25,29
[6]Journal of Medicinal Chemistry,1991,vol. 34,p. 1935 - 1943
[7]Journal of the Chemical Society. Perkin transactions II,1984,p. 499 - 502
[8]Patent: US5643878,1997,A
[9]Patent: US6372778,2002,B1 .Location in patent: Example 161
[10]Patent: US2004/6090,2004,A1 .Location in patent: Page/Page column 34
[11]Patent: US5585397,1996,A
[12]Patent: US5783701,1998,A
[13]Patent: US2015/11535,2015,A1 .Location in patent: Paragraph 0242-0243
[14]Patent: WO2015/3958,2015,A1 .Location in patent: Page/Page column 44; 45
[15]Patent: WO2017/140778,2017,A1 .Location in patent: Page/Page column 98
[16]Patent: EP3327021,2018,A1 .Location in patent: Paragraph 0211-0215

2
[ 23328-69-0 ]
[ 1828-66-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 624,p. 25,29

3
[ 1828-66-6 ]
[ 123-08-0 ]
[ 99856-62-9 ]

Reference： [1]Patent: DE1016656,1957,

4
[ 1828-66-6 ]
[ 107-11-9 ]
[ 98428-72-9 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2182,2184

5
[ 1828-66-6 ]
[ 18004-75-6 ]
[ 76495-40-4 ]

Reference： [1]Liebigs Annalen der Chemie,1982,vol. No. 9,p. 1656 - 1676

6
[ 1828-66-6 ]
[ 63-91-2 ]
[ 124278-39-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1032 - 1042
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 1935 - 1943

7
[ 1828-66-6 ]
[ 76824-86-7 ]
[ 142103-30-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2562 - 2572

8
[ 1828-66-6 ]
[ 74163-81-8 ]
[ 142103-29-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2562 - 2572

9
[ 1828-66-6 ]
[ 56891-59-9 ]
[ 105168-63-6 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 1676 - 1686

10
[ 1828-66-6 ]
[ 106-44-5 ]
N-(4-methylphenoxysulfonyl)-morpholine [ No CAS ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1984,vol. 20,p. 371 - 376

11
[ 1828-66-6 ]
[ 92-69-3 ]
[ 72119-33-6 ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1984,vol. 20,p. 371 - 376

12
[ 1828-66-6 ]
[ 106-48-9 ]
N-(4-chlorophenoxysulfonyl)-morpholine [ No CAS ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1984,vol. 20,p. 371 - 376

13
[ 1828-66-6 ]
[ 108-95-2 ]
[ 1141-98-6 ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1984,vol. 20,p. 371 - 376

14
[ 1828-66-6 ]
[ 148016-92-6 ]
[ 175846-22-7 ]

Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 199 - 209

15
[ 1828-66-6 ]
[ 61-90-5 ]
[ 179982-04-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3820 - 3828
[2]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1237 - 1240

16
[ 10024-89-2 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; In chloroform; for 6h;Reflux;	A solution of morpholine hydrochloride (6.0g, 49mmol) in CHCl3(20mL) and SO2Cl2(80mL) was heated under reflux for 6h, then evaporated under reduced pressure. The residue was dissolved in DCM, diluted with pet ether, filtered through Celite and evaporated to give crude morpholine-4-sulfonyl chloride23(77). A solution of 1-(4-chlorophenyl)piperazine (70) (48mg, 0.24mmol) in DCM (1mL) was treated with crude77(50mg, 0.27mmol) in DCM 3mL) and DIPEA (0.lmL). The mixture was stirred for 2h and diluted with DCM, washed with dilute aqueous Na2CO3and evaporated. The residue was dissolved in EtOAc, filtered through Celite, evaporated and triturated with iPr2O to give58(77%)

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3820 - 3828
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 967 - 977

17
[ 1828-66-6 ]
[ 1004763-36-3 ]
[ 1004763-35-2 ]

Yield	Reaction Conditions	Operation in experiment
20%	With triethylamine; In dichloromethane; at 20℃;	Triethylamine (0.35 ml, 2.52 mmol, 3 eq) and 4-morpholinesulfonyl chloride (0.3 g, 1.68 mmol, 2 eq) are added to a solution of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}- 4,5,6,7-tetrahydro[1 ,3]thiazolo[4,5-b]pyridine 68 (0.3 g, 0.84 mmol) in dichloromethane (3 ml) at room temperature under stirring in a stream of argon. The reaction mixture is stirred at room temperature overnight, then 4-morpholinesulfonyl chloride (0.3 g, 1.68 mmol, 2 eq) is added and the reaction mixture is stirred at room temperature for an additional 6 h. Water (3 ml) and an aqueous saturated solution of potassium carbonate are added. The layers are separated and the aqueous layer is extracted with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue is purified by chromatography over silicagel (gradient: <n="94"/>dichloromethane/methanol from 10:0 to 9:1 ) to afford 0.085 g of 2-{4-[3-(2- methylpyrrolidin-1-yl)propoxy]phenyl}-4-(morpholin-4-ylsulfonyl)-4,5,6,7- tetrahydro[1 ,3]thiazolo[4,5-b]pyridine as a yellow oil. Yield: 20 %. LC-MS (MH+): 507.

Reference： [1]Patent: WO2008/12010,2008,A1 .Location in patent: Page/Page column 92-93

18
[ 1828-66-6 ]
[ 160232-08-6 ]
C₂₃H₃₉N₃O₆S [ No CAS ]

Reference： [1]Patent: US6372778,2002,B1 .Location in patent: Example 161

19
[ 110-91-8 ]
[ 7791-25-5 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	In acetonitrile; for 24h;Heating / reflux;	Morpholine (0.436 mL, 5 mmol) was added slowly and with caution to a mixture of sulfuryl chloride (1.205 ml, 15 mmol) in 5 mL acetonitrile. Heated to reflux and stirred for 24 hours. After starting material consumed, solution concentrated to oil, azeotroped with toluene (2x), concentrated to give crude product 126 stored as a 2M solution in dichloromethane (0.999 g, 5 mmol, 100%.) 1H NMR (CD3SOCD3) 8 3.80 (br s, 4H), 3.28 (br s, 4H. ) MS: 186 (M+1)

Reference： [1]Patent: WO2004/35576,2004,A2 .Location in patent: Page 227

20
[ 1828-66-6 ]
C₄H₉NO₄S*C₃₅H₃₀FN₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		Trimethylsilyethyl ether 44 (0.027 g, 0.0457 mmol) was dissolved in 0.5 mL dry tetrahydrofuran. To this was added triethylamine (0.025 mL, 0.1828 mmol) and 1 M tetrabutylammonium fluoride solution in tetrahydrofuran (0.0915 mL, 0.0915 mmol.) Stirred at room temperature 10 minutes until starting material consumed. Diluted with dichloromethane, washed with washed with 1M HCl solution, saturated brine, concentrated to give crude. Dissolved in 0.5 mL dichloromethane, added catalytic dimethylaminopyridine, triethylamine (0.025 ml, 0.1828 mmol) and 2 M morpholine sulfamoyl chloride solution 126 in dichloromethane (0.05 g, 0.10 mmol) and stirred at room temperature. After 1.5 hours, starting material consumed. Diluted with dichloromethane, washed with saturated brine, concentrated organics to give crude. Chromatographed (10% to 40% ethylacetate/hexanes) to give product 127 (0.0199 g, 0.031 mmol, 68%.) 1H NMR (CDCl3) delta 9.07 (s, 1H), 8.35 (d, 1H), 8.09 (s, 1H), 7.75 (d, 4H), 7.56 (dd, 1H), 7.27 (m, 8H), 7.05 (dd, 2H), 4.82 (s, 2H), 4.46 (s, 2H), 3.81 (m, 4H), 3.75 (m, 4H), 3.48 (m, 4H), 3.27 (m, 4H. ) MS: 790 (M+1)

Reference： [1]Patent: WO2004/35576,2004,A2 .Location in patent: Page 227;228

21
[ 1828-66-6 ]
9-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine [ No CAS ]
9-bromo-2-chloro-5,6-dihydro-5-(4-morpholinylsulfonyl)-dibenzo[b,f]azocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In 1,1-dichloroethane; at 100℃; for 4h;	A solution of 9-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine (30 mg, 0.09 mmol) (prepared in a manner analogous to that described for Example 1F) in dichloroethane was treated with pyridine (0.02 mL, 0.27 mmol) and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (22 mg, 0.12 mmol). The reaction mixture was stirred at 100 C. for four hours then concentrated, diluted with MeOH and filtered. The crude product was purified by preparative reversed-phase HPLC to afford Example 338A (32 mg). HPLC Rt=3.89 min. m/z=469 (M+H+)

Reference： [1]Patent: US2005/250753,2005,A1 .Location in patent: Page/Page column 97

22
[ 108085-16-1 ]
[ 1828-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In 1,2-dichloro-ethane; at 80℃; for 18h;	EXAMPLE 9 Synthesis of 4-(2,6-dichloro-benzoylaminoVl-H-pyrazole-3-carboxylic acid ["1- Cmorpholine-4-sulphonyl')-piperidin-4vn-amideTo morpholinium chloride (0.5 g, 4 mmol), was added triethylamine (6 ml, 40 mmol) and the mixture was stirred for 15 minutes at room temperature. Chloroform was added (10 ml), the mixture was cooled to -5 0C and chlorosulphonic acid(0.266 ml, 4 mmol) was added dropwise so as to maintain the temperature below 0 0C. The chloroform was evaporated and the mixture was treated with 0.03 mol of NaOH in 16 ml of water. The solution was evaporated to dryness to afford morpholine-4-sodium sulphamate. The crude material was dissolved in 1,2- dichloroethane (5 ml) and POCl3 (0.7ml, 8mmol) was added. The reaction mixture was heated at 80 0C for 18 hours. Petroleum ether and EtOAc were then added to the mixture and solids were removed by filtration. The filtrate was evaporated to dryness to afford morpholine sulphamoyl chloride. The resulting crude material was dissolved in DCM (30 ml), triethylamine (1 ml, 10 mmol) was added followed by the addition of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid EPO <DP n="172"/>piperidin-4-ylamide hydrochloride (Preparation X) (1 g, 4 mmol) at 0 0C. The reaction mixture was stirred at room temperature for 16 hours, then added dioxane (5 ml) and heated at 50 C for 3 hours. The crude product was partitioned between EtOAc and water. The organic phase was dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by by flash chromatography on silica eluting with EtOAc: hexane 1 :2 to 100% EtOAc to afford the title compound as white solid (130 mg, 10% over 3 steps) (LC/MS: Rt 2.80, [M+H]+ 531).

Reference： [1]Patent: WO2006/77414,2006,A1 .Location in patent: Page/Page column 170-171

23
AT₇₅₁₉ [ No CAS ]
[ 1828-66-6 ]
4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid [1-(morpholine-4-sulphonyl)-piperidin-4yl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With triethylamine; In dichloromethane; at 0 - 50℃; for 18h;	EXAMPLE 9 Synthesis of 4-(2,6-dichloro-benzoylaminoVl-H-pyrazole-3-carboxylic acid ["1- Cmorpholine-4-sulphonyl')-piperidin-4vn-amideTo morpholinium chloride (0.5 g, 4 mmol), was added triethylamine (6 ml, 40 mmol) and the mixture was stirred for 15 minutes at room temperature. Chloroform was added (10 ml), the mixture was cooled to -5 0C and chlorosulphonic acid(0.266 ml, 4 mmol) was added dropwise so as to maintain the temperature below 0 0C. The chloroform was evaporated and the mixture was treated with 0.03 mol of NaOH in 16 ml of water. The solution was evaporated to dryness to afford morpholine-4-sodium sulphamate. The crude material was dissolved in 1,2- dichloroethane (5 ml) and POCl3 (0.7ml, 8mmol) was added. The reaction mixture was heated at 80 0C for 18 hours. Petroleum ether and EtOAc were then added to the mixture and solids were removed by filtration. The filtrate was evaporated to dryness to afford morpholine sulphamoyl chloride. The resulting crude material was dissolved in DCM (30 ml), triethylamine (1 ml, 10 mmol) was added followed by the addition of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid EPO <DP n="172"/>piperidin-4-ylamide hydrochloride (Preparation X) (1 g, 4 mmol) at 0 0C. The reaction mixture was stirred at room temperature for 16 hours, then added dioxane (5 ml) and heated at 50 C for 3 hours. The crude product was partitioned between EtOAc and water. The organic phase was dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by by flash chromatography on silica eluting with EtOAc: hexane 1 :2 to 100% EtOAc to afford the title compound as white solid (130 mg, 10% over 3 steps) (LC/MS: Rt 2.80, [M+H]+ 531).

Reference： [1]Patent: WO2006/77414,2006,A1 .Location in patent: Page/Page column 170-171

24
[ 1828-66-6 ]
[ 99-27-4 ]
[ 911790-21-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With pyridine; at 90℃;	2.5 g (11.7 mmol) dimethyl 5-amino-isophthalate were suspended in 40 ml of pyridine, slowly combined with 3.3 g (17.8 mmol) 13-a and stirred overnight at 90 C. Then the reaction solution was combined with 50 ml 4N HCl while cooling with an ice bath and the precipitate was filtered off. The crystals were dissolved in dichloromethane, filtered through a phase separation cartridge and the filtrate was evaporated down i. vac. Yield 2.7 g (64%) brown crystals 13-b. RT(HPLC 1)=4.30 min

Reference： [1]Patent: US2006/223759,2006,A1 .Location in patent: Page/Page column 219

25
[ 1828-66-6 ]
[ 540-37-4 ]
[ 914606-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 20℃; for 16h;	To a solution of 10 g of 4-iodoaniline (45.6 mmol) in 200 ml of acetonitrile there are added 6.41 ml of Et3N (45.6 mmol) and 8.47 g of morpholine-4-sulphonyl chloride (45.6 mmol). The reaction mixture is stirred for 16 hours at ambient temperature. The acetonitrile is evaporated off in vacuo, and the residue is taken up in 1N HCl and extracted with CH2Cl2. The organic phases are combined, washed with brine, dried (MgSO4) and treated with animal charcoal to yield the title product. Melting point: 91 C.

Reference： [1]Patent: US2006/258671,2006,A1 .Location in patent: Page/Page column 4

26
[ 1828-66-6 ]
[ 24313-88-0 ]
[ 68061-32-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With triethylamine; In water; ethyl acetate; benzene;	EXAMPLE 6 4-[N-(3,4,5-trimethoxyphenyl)-sulphamoyl]-morpholine. (C13 H20 N2 O6 S=332.38) To a solution of 4.8 g (0.026 mole) 3,4,5-trimethoxyaniline and 2.6 g (0.026 mole) triethylamine in 200 ml dry benzene are added 5.7 g (0.031 mole) N-chlorosulphonyl morpholine. The mixture obtained is heated at the reflux of the solvent, with stirring, for 14 hours. After evaporation of the solvent under vacuum, the oily residue is taken up in a mixture of water and ethyl acetate. The two phases are decanted, the organic phase washed with a 2 N-hydrochloric acid solution, dried and concentrated to dryness; the residual solid is triturated in ether and the insoluble material dried to give 4.1 g of a slightly coloured solid (47% yield). Purification is by recrystallisation from water. Melting point=148 C.

Reference： [1]Patent: US4252804,1981,A

27
[ 1828-66-6 ]
[ 211490-08-3 ]
[ 6674-22-2 ]
6-Methyl-3-[(morpholin-4-ylsulphonyl)amino]-2-oxo-4-(phenylmethyl)-1,2-dihydropyridine-1-acetic Acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane;	EXAMPLE 5 (compound No. 52) 6-Methyl-3-[(morpholin-4-ylsulphonyl)amino]-2-oxo-4-(phenylmethyl)-1,2-dihydropyridine-1-acetic Acid 1 ml (6.8 mmol) of morpholin-4-ylsulphonyl chloride and 1.1 ml (7.35 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene are added every three days for 15 days to 1.75 g (6.1 mmol) of methyl 3-amino-6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydropyridine-1-acetate in solution in 10 ml of dichloromethane. 100 ml of dichloromethane are then added to the reaction medium and the medium is washed successively with 20 ml of water, 100 ml of an aqueous hydrochloric acid solution and 20 ml of a saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica gel column, eluding with a dichloromethane:methanol (98:2) mixture and the product is recrystallized from ethanol. 1.4 g of product are obtained in the form of a white powder. Yield=52%; Melting point=160-162 C. The product obtained is hydrolyzed according to the procedure of Example 3 using 4.8 ml of a 1 N aqueous sodium hydroxide solution. 1.1 g of product are obtained. Melting point=158 C. (melting with decomposition).

Reference： [1]Patent: US6252082,2001,B1

28
[ 1828-66-6 ]
[ 57060-86-3 ]
methyl 2-(morpholinosulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethylmorpholine;; sodium hydrogencarbonate; citric acid; In tetrahydrofuran; chloroform; water;	26a Methyl 2-(morpholinosulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate With stirring, 4.2 g (0.025 mol) of morpholine-N-sulfonyl chloride in 20 ml of THF are added dropwise to a solution of 4.8 g (0.025 mol) of methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate and 2.9 g (0.025 mol) of N-ethylmorpholine. The mixture is stirred at RT for 2 h and then heated under reflux for another 2 h so that the reaction goes to completion. CHCl3 is added to the reaction solution, which is then treated with 5% strength citric acid, 5% strength NaHCO3 solution and water. The organic phase is dried over Na2SO4 and evaporated to dryness. Yield of ester (26a): 7.5 g (92% of theory)

Reference： [1]Patent: US6207672,2001,B1

29
[ 1828-66-6 ]
N-{4-(2-amino-4-thiazolyl)phenyl}-2-{(phenylmethyl)amino}-acetamide.2HCl [ No CAS ]
N-{4-(2-Amino-4-thiazolyl)phenyl}-2-{(4-morpholinylsulfonyl)-(phenylmethyl)amino}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With dmap; In dichloromethane; ethyl acetate;	Example 7 N-{4-(2-Amino-4-thiazolyl)phenyl}-2-{(4-morpholinylsulfonyl)-(phenylmethyl)amino}acetamide (1: R1, R2 and R3=H, R4=PhCH2, R5=4-morpholinylsulfonyl and Q=valance bond) 4-Morpholinesulfonyl chloride (213 mg, 1.15 mmol) was added (5 min) to an ice-cold solution of N-{4-(2-amino-4-thiazolyl)phenyl}-2-{(phenylmethyl)-amino}acetamide.2HCl (450 mg, 1.09 mmol), the corresponding free base has been described in example 2) and Et3N (443 mg, 4.38 mmol) in CH2Cl2 (10.9 mL). The reaction mixture was allowed to warm to room temperature and DMAP (14.0 mg, 0.11 mmol) was added. After standing for 37 h at room temperature, the mixture was dissolved in EtOAc (125 mL). The solution was washed successively with saturated aqueous NaHCO3 (50 mL) and brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. Purification of the resulting residue by flash chromatography (SiO2, EtOAc) gave the title compound (200 mg, 38% yield) as a white solid: M.p. 193-194; 1H NMR (400 MHz, DMSO-d6) delta10.02 (s, 1H), 7.73 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.7 Hz, 2H), 7.30-7.41 (m, 5H), 7.01 (s, 2H), 6.89 (s, 1H), 4.59 (s, 2H), 3.91 (s, 2H), 3.58 (t, J=4.6 Hz, 4H), 3.18 (t, J=4.6 Hz, 4H); MS (FAB) m/z 488 (MH)+; Anal. Calcd for C22H25N5O4S2: C, 54.19; H, 5.17; N, 14.36. Found: C, 53.63; H, 5.07; N, 14.34.

Reference： [1]Patent: US6288091,2001,B1

30
[ 1828-66-6 ]
[ 873533-12-1 ]
[ 873533-74-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃; for 48h;	Example 28: Preparation of [N-(morpholinyl)sulfonyl-N-[3-[[2-(4-methylphenyl)-5-methyloxazol-4-yl]methoxy]benzyl]amino]aceticacid; FSCStep 1: Preparation of [N-(morpholinyl)sulfonyl-N-(3-benzyloxybenzyl)]amino] acetic acid ethyl ester; 3 g (10 mmol) of [N-(3-benzyloxybenzyl)amino]acetic acid ethyl ester and 2.78 g (15 mmol) of N-(morpholinyl)sulfonyl chloride were dissolved in 50 ml of dichloromethane, and 1.62 g (16 mmol) of triethylamine was added thereto at room temperature, followed by stirring for 2 days. The resulting mixture was concentrated under a reduced pressure to remove the solvent, andthe residue was subjected to silica gel column chromatography (eluent:hexane/ethylacetate = 1/1) to obtain the title compound (3.77 g, 84%).

Reference： [1]Patent: WO2006/6832,2006,A1 .Location in patent: Page/Page column 56-57

31
[ 1828-66-6 ]
C₁₃H₁₃BrClNO₂ [ No CAS ]
C₁₇H₂₀BrClN₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	EXAMPLE 4; One equivalent of benzopyran derivative in THF and 1 equivalent of sulfamoylchloride derivative in THF were reacted overnight at room temperature in the presence of 1.1 equivalent of triethylamine. The reaction mixture was evaporated and purified by liquid/liquid extraction with 10% tartatic acid and ethyl acetate. The organic layers were dried on sodium carbonate and evaporated. The LC-MS data are summarized below.
	With triethylamine; In tetrahydrofuran; at 20℃;	Example 4; 1 equivalent of benzopyrane derivative in THF and 1 equivalent of sulfamoylchlo- ride derivative in THF were reacted at room temperature over night in the presence of 1.1 equivalent of triethylamine. The reaction mixture was evaporated and purified by liquid/liquid extraction with 10% tartatic acid and ethyl acetate. The organic layers were dried on sodium carbonate and evaporated. The LC-MS data are summarized below.

Reference： [1]Patent: US2007/117823,2007,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2007/54580,2007,A1 .Location in patent: Page/Page column 38-39

32
[ 1828-66-6 ]
[ 1010816-09-7 ]
[ 1010816-05-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 861 - 874

33
[ 1828-66-6 ]
[ 959983-12-1 ]
[ 1045705-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 19.5h;	EXAMPLE 29 8-Cyclohexyl-N-(dimethylsulfamoyl)-11-methoxy-1a-((4-morpholinylsulfonyl)amino)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide. To the hydrochloride salt of 1a-amino-8-cyclohexyl-N-((dimethylamino)sulfonyl)-11-(methyloxy)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide (30 mg, 53.7 pmol) at r.t. under N2 was added a solution of <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (32 mg, 172 mumol) in DMF (1 ml total), and then triethylamine (41 mul, 294 mumol). The mixture was stirred at r.t. for 19.5 h. The mixture was then concentrated, diluted with MeOH and purified by Shimadzu-VP preparative reverse phase HPLC with separation method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=6 min, Flow Rate=30 mL/min, Column: Xterra Prep MS C18 5 u 3050 mm, Fraction Collection: 6.99-7.58 min. (UV detection at 220 nm) to give 8-cyclohexyl-N-(dimethylsulfamoyl)-11-methoxy-1a-((4-morpholinylsulfonyl)amino)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide. Analytical HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Flow Rate=5 ml/min, Column: Xterra MS C18 S7 3.050 mm; LC/MS: (ES+) m/z (M+H)+=672.12, HPLC Rt=1.892 min.

Reference： [1]Patent: US2008/188458,2008,A1 .Location in patent: Page/Page column 52-53

34
[ 1828-66-6 ]
[ 1055306-88-1 ]
[ 1055307-49-7 ]

Yield	Reaction Conditions	Operation in experiment
78%		Reference Example 136; tert-butyl { [4-fluoro-5- (2-fluoropyridin-3-yl) -1- (morpholin-4- ylsulfonyl) -lH-pyrrol-3-yl]methyl Jmethylcarbamate; To a solution of tert-butyl { [4-fluoro-5- (2- fluoropyridin-3-yl) -lH-pyrrol-3-yl]methyl}methylcarbamate (324 mg) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 121 mg) at room temperature, and the mixture was stirred for 10 min. 15-Crown-5 (664 mg) was added, morpholine- 4-sulfonyl chloride (250 mg) was added and the mixture was further stirred for 2 hr. The reaction mixture was diluted with water, 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=4 : 1-»3:2) to give the title compound as a colorless oil (yield 370 mg, 78%) .1H-NMR (CDCl3) delta: 1.48 (9H,s), 2.92(7H,br), 3.57 (4H, t, J=4.7Hz) , 4.30(2H,s), 7.13(lH,br), 7.26-7.30 (IH,m) , 7.83-7.96 (lH,m) , 8.27 ( IH, d, J=4.5Hz) .

Reference： [1]Patent: WO2008/108380,2008,A2 .Location in patent: Page/Page column 154

35
[ 1828-66-6 ]
[ 865062-64-2 ]
4a-(4-fluoro-benzyl)-1-(4-fluoro-phenyl)-6-(morpholine-4-sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1312 - 1317

36
[ 1828-66-6 ]
[ 1083322-87-5 ]
[ 1083324-02-0 ]

Yield	Reaction Conditions	Operation in experiment
18%	With pyridine; at 20 - 50℃; for 135.5h;	Example 190; Preparation of N-{5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinyl}-4-morpholinesulfonamide; In an oven-dried flask under nitrogen, a solution of 5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinamine (99 mg, 0.327 mmol) in pyridine (3 mL) at room temperature was treated with <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (96 mg, 0.491 mmol) by syringe. The reaction was stirred at room temperature for 16.5 hours. The reaction was very sluggish so the reaction was placed in an oil bath at 50 C. and stirred at that temperature for 23 hours. The reaction was progressing to the desired product as determined by LCMS but was not yet complete. The reaction mixture was stirred for an additional 4 days at 50 C. The reaction did not progress to completion. The reaction was cooled to room temperature and concentrated in vacuo. The residue was taken up into 200 mL ethyl acetate and 50 mL water. The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL) followed by brine (100 mL), dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography eluting with 0-10% methanol in dichloromethane provided the desired product as a residue which was not pure. Addition of dichloromethane/ether resulted in precipitate formation. The precipitate was collected by filtration. Recrystallization of the precipitate from ethanol provided the title compound (26 mg, 18%) as a rust-coloured solid. MS (ES)+ m/e 452.0 [M+H]+.

Reference： [1]Patent: US2008/293706,2008,A1 .Location in patent: Page/Page column 61-62

37
[ 1828-66-6 ]
[ 1118605-23-4 ]
C₂₈H₅₂N₄O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 209 - 213

38
[ 1828-66-6 ]
[ 1160508-82-6 ]
[ 1160508-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h;	Morpholine-4-sulfonyl chloride (0.119 mmol) is added to a solution of 3-propyl-5-(cyclohexylmethyl-piperidin-4-ylmethyl-amino)- 1 -methyl- 1 ,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (0.099 mmol) and N,N-diisopropylethylamine (0.199 mmol) in dichloromethane (1 mL) and it is stirred at room temperature for 18h. After completion of the reaction (monitored by LCMS), the solvent is removed under reduced pressure and the final compound is isolated by preparative HPLC. [00380] Preparative HPLC: Waters XBridge Prep C 18 5mum ODB 19mm ID x 100mm L. The method uses MeCN/H2O 55-80% gradients. H2O contains 0.1% Trifluoroacetic acid (TFA).

Reference： [1]Patent: WO2009/71707,2009,A1 .Location in patent: Page/Page column 57-58

39
[ 1828-66-6 ]
[ 2450-71-7 ]
[ 90809-93-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2719 - 2730

40
[ 1828-66-6 ]
[ 1195768-16-1 ]
[ 1195768-81-0 ]

Yield	Reaction Conditions	Operation in experiment
13.8%	With pyridine; at 20℃; for 12h;	Example 37; N-{3-[2-(1-Methylethyl)-5-(2-[2-(methylsulfonyl)ethyl]amino}-4-pyrimidinyl)-1,3-thiazol-4-yl]phenyl}-4-morpholinesulfonamide trifluoroacetic acid salt; Step A: N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-4-morpholinesulfonamide; To a solution of 3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]aniline (1.5 g, 4.5 mmol) in pyridine (15 mL) was added <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (1.26 g, 6.8 mmol). The reaction was stirred at rt for 12 h. Then the reaction was washed with water (50 mL), and extracted with DCM (2×50 mL). The organic layer was washed with brine, dried over anhydrous NaSO4, filtrated and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (DCM:EtOAc 60:1) to afford the title compound of Step A (297 mg, 13.8% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.30 (d, J=5.3 Hz, 1H), 7.27-7.36 (m, 2H), 7.21-7.26 (m, 2H), 6.98 (d, J=5.3 Hz, 1H), 3.58-3.64 (m, 4H), 3.22-3.33 (m, 1H), 3.14-3.21 (m, 4H), 1.40 (d, J=7.0 Hz, 6H). MS (ES+): 480 [M+H]+.

Reference： [1]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 81

41
[ 1828-66-6 ]
[ 1188528-92-8 ]
[ 1188529-42-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; triethylamine; In 1,2-dichloro-ethane; at 20 - 50℃; for 50h;	Methyl 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (97 mg, 0.50 mmol) was suspended in 4 mL of DCE and sequentially treated with DMAP (61 mg, 0.50 mmol) and triethylamine (0.077 mL, 0.55 mmol). Morpholine-4-sulfonyl chloride (102 mg, 0.55 mmol) was added and the mixture was stirred at ambient temperature for 2 hours and then heated to 50 C. for 2 days. The mixture was cooled to ambient temperature and diluted with 10 mL of DCM and the whole solution poured into 15 mL of 1M aqueous H3PO4. The layers were separated and the aqueous layer was extracted with 10 mL of DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by normal phase flash chromatography (gradient elution 50% to 100% EtOAc/Hexanes) to provide 88 mg (51%) of the title compound as a thick tan oil. 1H NMR (CDCl3) delta 8.59 (d, 1H), 8.34 (d, 1H), 4.48 (m, 2H), 3.86 (s, 3H), 3.77 (m, 2H), 3.69 (m, 4H), 3.26 (m, 4H). LCMS (+ESI) m/z=344.1 [M+H]+.

Reference： [1]Patent: US2009/247502,2009,A1 .Location in patent: Page/Page column 25

42
[ 684284-66-0 ]
[ 1828-66-6 ]
C₄H₉NO₄S*C₃₅H₃₀FN₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		Trimethylsilylethyl ether 44 (0.027 g, 0.0457 mmol) was dissolved in 0.5 mL dry tetrahydrofuran. To this was added triethylamine (0.025 mL, 0.1828 mmol) and 1 M tetrabutylammonium fluoride solution in tetrahydrofuran (0.0915 mL, 0.0915 mmol. ) Stirred at room temperature 10 minutes until starting material consumed. Diluted with dichloromethane, washed with washed with 1M HCl solution, saturated brine, concentrated to give crude. Dissolved in 0.5 mL dichloromethane, added catalytic dimethylaminopyridine, triethylamine (0.025 mL, 0.1828 mmol) and 2 M morpholine sulfamoyl chloride solution 126 in dichloromethane (0.05 g, 0.10 mmol) and stirred at room temperature. After 1.5 hours, starting material consumed. Diluted with dichloromethane, washed with saturated brine, concentrated organics to give crude. Chromatographed (10% to 40% ethylacetate/hexanes) to give product 127 (0.0199 g, 0.031 mmol, 68%. ) ¹H NMR (CDCl3) No. 9.07 (s, 1H), 8.35 (d, 1H), 8.09 (s, 1H), 7.75 (d, 4H), 7.56 (dd, 1H), 7.27 (m, 8H), 7.05 (dd, 2H), 4.82 (s, 2H), 4.46 (s, 2H), 3.81 (m, 4H), 3.75 (m, 4H), 3.48 (m, 4H), 3.27 (m, 4H. ) MS: 790 (M+l)

Reference： [1]Patent: WO2005/117904,2005,A2 .Location in patent: Page/Page column 464

43
[ 74115-13-2 ]
[ 1828-66-6 ]
[ 1202552-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; In acetone; at 0 - 20℃;	A flask is charged with 5-bromo-pyridin-3-ol (0.31O g, 1.78 mmol), potassium phosphate (0.982 g, 4.63 mmol) and acetone (10 ml_), and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (0.529 g, 2.85 mmol) is added dropwise at 0 0C. The mixture is stirred at room temperature overnight. Saturated NaHCO3 in water (1 ml_) is added and the mixture is concentrated in vacuo. The residue is purified on silica gel chromatography eluting with a 9:1 to 4:1 heptane-ethyl acetate gradient to give morpholine-4-sulfonic acid 5-bromo-pyridin-3-yl ester. MS (ESI) m/z 322.9 and 324.9 (M+H)+.

Reference： [1]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 166

44
[ 1828-66-6 ]
C₂₀H₂₀ClF₂NO₃S [ No CAS ]
[ 1237802-28-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3632 - 3635

45
[ 1828-66-6 ]
N₆-cyclohexyl-N₂-(2-methoxy-4-piperazin-1-yl-phenyl)-9H-purine-2,6-diamine dihydrochloride [ No CAS ]
[ 1246531-36-1 ]

Yield	Reaction Conditions	Operation in experiment
		[00610] To a solution of the bis-HCl salt of N6-cyclohexyl-N2-(2-methoxy-4- piperazin- l-yl-phenyl)-9H-purine-2,6-diamine 106 (100 mg, 0.20 mmol) in DMF (2 mL) was added DIEA (0.1 mL, 0.67 mmol). After stirring for 5 minutes the desired sulfonyl chloride reagent (0.22 mmol) was added. The reaction was allowed to stir over the weekend, the solvents removed, and the residue was purified by reverse phase flash chromatography with MeOH/H2O/0.1%TFA as eluant to provide the desired product C196.

Reference： [1]Patent: WO2010/111406,2010,A2 .Location in patent: Page/Page column 142

46
[ 1828-66-6 ]
[ 1255644-54-2 ]
[ 1255649-34-3 ]

Yield	Reaction Conditions	Operation in experiment
		4-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.646 g) dissolved in methylene chloride (10 ml) under an argon atmophere were treated with DMAP (0.673 g at RT, the mixture was cooled to 00C and morpholine-4-sulfonylchloride (0613 g) in methylene chloride (2 ml) was added dropwise. The mixture was stirred for 12 h at RT then partitioned between methylen chloride and 1 M HCl. The layers were separated, the organic layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, the residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 50%) to give 4-(2-methoxy-ethyl)-l-(morpholine-4-sulfonyl)-piperidine-4- carboxylic acid ethyl ester, (0.68 g) as a light yellow solid. MS (ESI): 365.17 (MH+).

Reference： [1]Patent: WO2010/130665,2010,A1 .Location in patent: Page/Page column 65

47
[ 1828-66-6 ]
[ 1262786-55-9 ]
[ 1262786-34-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 35℃; for 19.5h;Inert atmosphere;	Example 12: Lambda/-{4-r(1R5SV3-(2-methyl-1H-benzimidazol-1-vn-8- azabicvclobeta^.iloct-delta-yll^-phenylbutylM-morpholinesulfonamideTo a solution of intermediate 6 (61 mg, 0.16 mmol) in dry CH2CI2 (2 ml.) was added diisopropylethylamine (0.070 ml_, 0.4 mmol). A solution of 4- morpholinesulfonyl chloride (0.022 ml_, 0.16 mmol) was added and the reaction stirred at room temperature under nitrogen atmosphere for 1.5 h and then heated to 35 0C for 18 h. The reaction was concentrated in vacuo and purified by reverse-phase HPLC eluting with 10-90% water/acetonitrile/0.1% TFA. to give the title compound (55 mg, 64% yield) as a white solid (free-based with K2CO3). 1 H NMR (400 MHz, DMSOd6) d ppm 7.50 (d, J=7.42 Hz, 1 H) 7.39 (br. s., 3 H) 7.32 (d, J=7.42 Hz, 3 H) 7.18 - 7.29 (m, 4 H) 7.05 - 7.18 (m, 3 H) 4.64 (br. s., 1 H) 3.01 - 3.23 (m, 3 H) 2.78 - 3.01 (m, 5 H) 2.53 (s, 3 H) 2.29 - 2.46 (m, 3 H) 1.90 - 2.1 1 (m, 3 H) 1.74 - 1.88 (m, 3 H) 1.59 - 1.73 (m, 4 H) ). HRMS: (M + H)+ calcd for C29H39N5O3S + H, 538.2852; found, 538.2849

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1394 - 1398
[2]Patent: WO2011/11652,2011,A1 .Location in patent: Page/Page column 32-33

48
[ 1126-09-6 ]
[ 1828-66-6 ]
[ 702669-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	Piperidine-4-carboxylic acid ethyl ester (0.943 g) dissolved in methylene chloride (60 ml) under an argon atmosphere was treated at RT, first with 4-dimethylaminopyridine (1.465 g) then dropwise with <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (1.136 g) and the reaction mixture was stirred for 12 h at RT to complete the reaction. The reaction mixture was then partitioned between methylene chloride and aqueous 1N HCL, the layers were separated and the organic layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, to give 1-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (1.9 g) as a light yellow solid which was directly used in the next step.
	With dmap; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	Piperidine-4-carboxylic acid ethyl ester (0.943 g) dissolved in methylene chloride (60 ml) under an argon atmosphere was treated at RT, first with 4-dimethylaminopyridine (1.465 g) then dropwise with <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (1.136 g)and the reaction mixture was stirred for 12 h at RT to complete the reaction. The reaction mixture was then partitioned between methylene chloride and aqueous IN HCL, the layers were separated and the organic layer washed with 2M aqueous KHCO3 then dried over Na2S04. The solvent was evaporated off, to give l-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (1.9 g) as a light yellow solid which was directly used in the next step.

Reference： [1]Patent: US2011/65707,2011,A1 .Location in patent: Page/Page column 27
[2]Patent: WO2011/29808,2011,A1 .Location in patent: Page/Page column 74

49
[ 1828-66-6 ]
[ 1292310-65-6 ]
[ 1292310-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20 - 55℃;	A solution of 5-[2-({4-[2-(2-aminoethoxy)ethoxy]-3- methoxyphenyl}amino)pyrimidin-4-yl]-2-(tetrahydro-2H-pyran-4-yloxy)benzonitrile (18 mg, 0.037 mmol), Et3N (0.25 mL) and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (7 mu) in THF (2 mL) was stirred at rt for 2 h. The reaction was heated to 55 C o/n. The reaction was concentrated onto Celite and purified by RP-MPLC (Cis, MeOH/H20, 0-100%, w/ 0.1% TFA) to provide the title compound. 1H NMR (DMSO- e) delta 9.56 (s, IH), 8.56 (d, IH), 8.52 (dd, IH), 8.44 (dd, IH), 7.66 (br s, IH), 7.54 (d, IH), 7.48-7.40 (m, 2H), 7.20 (d, IH), 6.92 (d, IH), 4.95 (sept, IH), 4.08-4.02 (m, 2H), 3.92-3.3 (m, 2H), 3.81 (s, 3H), 3.75-3.70 (m, 2H), 3.63-3.57 (m, 5H), 3.57-3.50 (m, 3H), 3.10 (q, 2H), 3.04-2.97 (m, 4H), 2.10-1.98 (m, 2H), 1.62-1.74 (m, 2H); LC-MS [M+H]+ 655.2525.

Reference： [1]Patent: WO2011/46970,2011,A1 .Location in patent: Page/Page column 152; 153

50
[ 1828-66-6 ]
[ 1353622-83-9 ]
[ 1353623-01-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; at 20 - 70℃;	Compound 15To a solution of compound 3 (13 mg, 0.036 mmol) in pyridine (1.0 mL) was added 4- Morpholinesulfonyl chloride (67mg, 0.36 mmol) at RT, The reaction was heated at 70 overnight. The volatile were removed under reduced pressure at 40C and the resulting residue was purified by preparative HPLC (MeCN in H20 with a gradient from 0% to 95%) to afford compound 15 (12 mg, 67%) as a white powder after lyophilization.1 H-NMR (CD3CN, 300 MHz): delta 9.84 (s, IH), 7.64 (d, J= 9.3 Hz, IH), 7.46 (d, J= 8.1 Hz, IH), 7.22 (s, IH), 5.98 (s, IH), 3.60 (t, J= 4.5 Hz, IH), 3.22 (t, J= 4.5 Hz, IH), 2.32-2.30 (m, 4H), 2.05 (s, 3H), 1.96 (s, 3H), 1.75-1.64 (mc, 5H).LCMS m/z [M+H]+ C24H3oN605S requires: 515.60. Found 515.04HPLC Tr (min), purity %: 2.23, 98%

Reference： [1]Patent: WO2011/163518,2011,A1 .Location in patent: Page/Page column 181-182

51
[ 1828-66-6 ]
[ 1383987-90-3 ]
[ 1383988-10-0 ]

Yield	Reaction Conditions	Operation in experiment
9.89%	With pyridine; at 20℃; for 18h;	EXAMPLE 70N-[5-(2-amino-4-oxo-3^henyl-3,4-dihydro-6-quinazolinyl)-2-(methyloxy)-3-py dmmorpholinesulfonainide[00268] A solution of 4-morpholinesulfonyl chloride (155 mg, 0.835 mmol) and 2-amino-6- [5-amino-6-(methyloxy)-3-pyridinyl]-3-phenyl-4(3H)-quinazolinone (50 mg, 0.139 mmol) in pyridine (1 mL) was maintained at room temperature for 18 hours. The resulting mixture was treated with MeOH (1 mL) and concentrated. The residue was dissolved in DMF and purified by HPLC (10-90% CH3CN/H20, both containing 0.1 % formic acid) to obtain N-[5-(2-amino-4-oxo-3- phenyl-3,4-dihydro-6-quinazolinyl)-2-(methyloxy)-3-pyridinyl]-4-morpholinesulfonamide (7 mg, 0.014 mmol, 9.89% yield) as a white solid: H NMR (400 MHz, DMSO-d6) delta ppm 3.02 - 3.1 1 (m, 4 H) 3.51 - 3.61 (m, 4 H) 3.97 (s, 3 H) 6.38 (br. s., 2 H) 7.31 - 7.43 (m, 3 H) 7.48 - 7.63 (m, 3 H) 7.90 (d, J=2.24 Hz, 1 H) 7.91 - 7.96 (m, 1 H) 8.05 (d, J=2.24 Hz, 1 H) 8.30 (d, J=2.15 Hz, 1 H) 9.20 - 10.05 (m, 1 H); ES LC-MS m/z =509.1 ( +H)+.

Reference： [1]Patent: WO2012/87938,2012,A1 .Location in patent: Page/Page column 205-206

52
[ 588729-99-1 ]
[ 1828-66-6 ]
[ 1162680-93-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5714 - 5720

53
[ 273-53-0 ]
[ 1828-66-6 ]
[ 21326-90-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium dichromate; dichloro(2,2'-bipyridine)palladium(II); copper(l) cyanide; potassium carbonate; In chlorobenzene; at 150℃; for 24h;Sealed tube; Molecular sieve;	General procedure: Under air, a reaction tube was charged with benzoxazole (0.2 mmol), dimethylsulfamoyl chloride (0.3 mmol), BipyPdCl2 (10 mol %), CuCN (20 mol %), K2CO3 (0.4 mmol), K2Cr2O7 (0.2 mmol) and dry PhCl (2 mL). The mixture was stirred at 150 o C for 24 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6297 - 6299,3

54
[ 934-32-7 ]
[ 1828-66-6 ]
[ 50435-23-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide; In water; acetonitrile; at 20℃;	Step A1-(morpholinosulfonyl)-1H-benzo[d]imidazol-2- [00397] A solution of 1 H-benzo[d]imidazol-2-amine (0.36 g, 2.70 mmol) in CH3CN (10 mL) and water (1 mL) was treated with sodium hydroxide (0.238 g, 5.95 mmol). After everything dissolved <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (0.502 g, 2.70 mmol) was added and the mixture was stirred at room temperature overnight. The resulting slurry was filtered, solid washed with CH3CN to obtain 1-(morpholinosulfonyl)-1 H-benzo[d]imidazol-2-amine (557 mg, 1.973 mmol, 73.0 % yield) as a white solid: 1H NMR (400 MHz, DMSO-cfe) delta ppm 3.20 - 3.29 (m, 4 H) 3.49 - 3.58 (m, 4 H) 6.91 (s, 2 H) 6.97 - 7.05 (m, 1 H) 7.11 - 7.19 (m, 1 H) 7.19 - 7.27 (m, 1 H) 7.52 (d, =8.00 Hz, 1 H); ES LC-MS m/z =283.07 (M+H)+.

Reference： [1]Patent: WO2012/174312,2012,A2 .Location in patent: Page/Page column 280-281

55
[ 1828-66-6 ]
C₁₄H₁₄N₂S*ClH [ No CAS ]
C₁₈H₂₁N₃O₃S₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4037 - 4043

56
[ 1828-66-6 ]
[ 1380228-73-8 ]
[ 1380228-98-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With pyridine; In dichloromethane; at 50℃; for 2h;	The 2,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine (50 mg, 0.120 mmol) prepared at Step 9 was added and dissolved into dichloromethane solvent. <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (24 mg, 0.130 mmol) and pyridine (11 uL, 0.130 mmol) were added into the reaction solution and stirred at 50C for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 59 mg of the target compound, N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)morpholine-4-sulfonamide (percentage yield: 86%), was obtained.1H NMR(400MHz, CDCl3): delta 11.62(s, 1H), 9.66(dd, J = 8.0, 1.6 Hz, 1H), 9.05(s, 1H), 8.40(s, 1H), 8.30(dd, J = 4.4, 1.6 Hz, 1H), 7.43(m, 1H), 7.02(m, 2H), 6.58(bs, 1H), 5.91(dd, J = 10.4, 2.4 Hz, 1H), 4.24(m, 1H), 3.85(m, 1H), 3.71(m, 2H), 3.28(m, 2H), 2.23-1.73(m, 6H).

Reference： [1]Patent: EP2647637,2013,A2 .Location in patent: Paragraph 0147

57
[ 1828-66-6 ]
[ 38212-33-8 ]
[ 1548117-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h;	A solution of morpholine hydrochloride (6.0g, 49mmol) in CHCl3(20mL) and SO2Cl2(80mL) was heated under reflux for 6h, then evaporated under reduced pressure. The residue was dissolved in DCM, diluted with pet ether, filtered through Celite and evaporated to give crude <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong>23(77). A solution of 1-(4-chlorophenyl)piperazine (70) (48mg, 0.24mmol) in DCM (1mL) was treated with crude77(50mg, 0.27mmol) in DCM 3mL) and DIPEA (0.lmL). The mixture was stirred for 2h and diluted with DCM, washed with dilute aqueous Na2CO3and evaporated. The residue was dissolved in EtOAc, filtered through Celite, evaporated and triturated with iPr2O to give58(77%), mp (EtOAc/pet ether) 152-153C.1H NMR (CDCl3)delta7.26 (br d,J=9.0Hz, 2H), 6.97 (br d,J=9.1Hz, 2H), 3.66-3.58 (m, 4H), 3.33-3.22 (m, 4H) after D2O, 3.20-3.11 (m, 8H). HPLC purity 98.2%.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 967 - 977

58
[ 1828-66-6 ]
C₁₈H₁₆ClN₃O [ No CAS ]
[ 1567372-98-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2053 - 2056

59
[ 1828-66-6 ]
4-(5-fluoro-2-methoxyphenyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride [ No CAS ]
4-(5-fluoro-2-methoxyphenyl)-2-[1-(morpholin-4-ylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	To a suspension of Example 87D (59 mg, 0.182 mmol) in methylene chloride (4 mL) was added <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (51 mg, 0.274 mmol) and triethyl amine (0.076 mL). The mixture was stirred at room temperature overnight and was directly separated by flash chromatography (0-15% CH3OH in CH2C12) to provide the title compound. H NMR (400 MHz, DMSO-d6): delta2.57 (s, 2 H), 3.1 1 - 3.14 (m, 4 H), 3.45 (t, J=5.65 Hz, 2 H), 3.59 - 3.64 (m, 4 H), 3.74 (s, 3 H), 3.96 (d, J=2.75 Hz, 2 H), 6.27 (d, J=1.83 Hz, 1 H), 6.52 (s, 1 H), 7.04 (d, J=5.19 Hz, 1 H), 7.18 - 7.29 (m, 3 H), 8.21 (d, J=5.19 Hz, 1 H), 1 1.87 (d, J=1.22 Hz, 1 H); MS (DCI/NH3) m/z 473 (M+H)+.

Reference： [1]Patent: WO2014/139328,2014,A1 .Location in patent: Page/Page column 581

60
[ 1828-66-6 ]
[ 76-05-1 ]
[ 177906-48-8 ]
C₁₀H₂₁N₃O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Stage 2: A mixture of Intermediate XV.1 stage 1 (173.2 mg; 0.93 mmol) and trans-(4-aminocyclohexyl)-carbamic acid tert-butylester (200.0 mg; 0.93 mmol) and DIPEA (171.2 muL; 1.00 mmol) in ACN (5 mL) is stirred at reflux for 8 hours. The solvent is removed. The residue is taken up in DCM and washed with water. The organic layer is separated and evaporated. The residue is taken up in TFA (3 mL) and stirred at r.t. for 2 hours. The solvent is removed. [0245] C10H21N3O3S*C2HF3O2
		Stage 1: Morpholine (0.50 mL; 5.74 mmol) and sulfuryl chloride (1.50 mL; 18.50 mmol)in ACN (5 mL) are stirred at reflux for 24 hours. The solvent is removed and the residue is taken up in toluene, treated with activated charcoal and filtered off. The solvent is reremoved.C4H8CLNO3S Stage 2: A mixture of Intermediate XV.1 stagel (173.2 mg; 0.93 mmol) and trans-(4- aminocyclohexyl)-carbamic acid tert-butylester (200.0 mg; 0.93 mmol) and DIPEA (171.2 jiL; 1.00 mmol) in ACN (5 mL) is stirred at reflux for 8 hours. The solvent is removed. The residue is taken up in DCM and washed with water. The organic layer is separated and evaporated. The residue is taken up in TFA (3 mL) and stirred at r.t. for 2 hours. Thesolvent is removed.C10H21N3035 * C2HF302

Reference： [1]Patent: US2015/11535,2015,A1 .Location in patent: Paragraph 0241; 0244-0245
[2]Patent: WO2015/3958,2015,A1 .Location in patent: Page/Page column 44; 45

61
[ 1828-66-6 ]
ethyl 7-(1,3-dimethyl-5-((4-(piperazin-1-yl)phenoxy)-methyl)-1H-pyrazol-4-yl)-1-(2-morpholinoethyl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate [ No CAS ]
7-(1,3-dimethyl-5-((4-(4-(morpholinosulfonyl)piperazin-1-yl)phenoxy)methyl)-1H-pyrazol-4-yl)-1-(2-morpholinoethyl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2180 - 2194

62
[ 1828-66-6 ]
[ 3964-86-1 ]
N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 25℃; for 2h;	A solution of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine hydrochloride (0.141 g, 0.489 mmol) in DMF (1.0 mL) was cooled to 0 C and treated sequentially with triethylamine (142 L, 1.027 mmol) and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (0.100 g, 0.539 mmol). The solution was warmed to 25 C and stirred for 2 h. The mixture was poured over saturated aqueous NaCl (20 mL) and extracted with CH2Cl2 (3 50 mL). The combined organic layers were washed with saturated aqueous NaCl (3 50 mL), dried (Na2SO4), concentrated in vacuo, and the residue was purified by flash chromatography (SiO2, 0-20% ethyl acetate-hexanes) to afford the title compound as a clear film (0.0969 g, 49%). 1H NMR (600 MHz, CDCl3) 7.16 (2H, t, J = 7.8 Hz), 7.13 (2H, d, J = 7.8 Hz), 7.08 (2H, d, J = 7.8 Hz), 6.96 (2H, t, J = 7.8 Hz), 4.58 (1H, t, J = 6.0 Hz), 3.82 (2H, t, J = 5.4 Hz), 3.58-3.62 (4H, s), 3.18-3.20 (4H, m), 3.10 (2H, q, J = 6.6 Hz), 3.02-3.05 (4H, m), 1.82 (2H, quintet, J = 6.0 Hz); 13C NMR (150 MHz, CDCl3) 148.0, 134.3, 130.2, 126.6, 123.0, 119.8, 66.2, 47.5, 46.1, 41.7, 32.2, 28.0; LCMS m/z 402.3 ([M + H+], C21H27N3O3S requires 402.2).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6528 - 6534

63
[ 1828-66-6 ]
3-(pyrrolidin-3-yloxy)-2,4'-bipyridine [ No CAS ]
3-((1-(morpholin-4-ylsulfonyl)pyrrolidin-3-yl)oxy)-2,4'-bipyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 mg	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	Example 85 3-((1-(morpholin-4-ylsulfonyl)pyrrolidin-3-yl)oxy)-2,4'-bipyridine To a mixture of 3-(pyrrolidin-3-yloxy)-2,4'-bipyridine (100 mg), triethylamine (0.17 mL) and DMF (2.0 mL) was added <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (120 mg) at 0 C., and the mixture was stirred at room temperature for 2 hr. The mixture was diluted with saturated brine, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (60 mg). 1H NMR (300 MHz, DMSO-d6) b 2.08-2.20 (1H, m), 2.22-2.36 (1H, m), 2.95-3.08 (4H, m), 3.33-3.57 (7H, m), 3.58-3.69 (1H, m), 5.25 (1H, brs), 7.47 (1H, dd, J=8.5, 4.5 Hz), 7.70 (1H, dd, J=8.5, 1.1 Hz), 7.86-7.94 (2H, m), 8.35 (1H, dd, J=4.5, 1.1 Hz), 8.59-8.69 (2H, m).

Reference： [1]Patent: US2016/24049,2016,A1 .Location in patent: Paragraph 0810; 0811

64
9-benzyl-3-methylene-1-tosyl-1,5,9-triazacyclododecane [ No CAS ]
[ 1828-66-6 ]
9-benzyl-3-methylene-1-(N-morpholinosulfonyl)-5-(p-toluenesulfonyl)-1,5,9-triazacyclododecane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2633 - 2647

65
[ 1828-66-6 ]
C₁₉H₁₈NO₃⁽¹⁺⁾*Cl^(1-) [ No CAS ]
C₂₃H₂₈N₂O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90 mg		To a 25mL round bottom flask was added DMF (3mL), in an ice bath with stirring was added sodium hydride (39mg, 1.61mmol), stirred for 5min, and then added portionwise compound E (300mg, 0.874mmol), stirred for 15min under ice bath, then at room temperature stirred for 1h, followed by morpholin-N-sulfonyl chloride F (324mg, 1.75mmol), the addition was completed, the reaction at room temperature overnight, the solvent was distilled off under reduced pressure, to give a paste G which was used directly in the next reaction. To a 100mL round bottom flask the crude G was dissolved in methanol (10 mL), stirred under an ice bath, portionwise added with sodium borohydride (121mg, 3.21 mmol), the addition was completed, the reaction at room temperature for 30min, the reaction solution was spin dry, the residue in water and ethyl acetate, the organic phase dried over anhydrous sodium sulfate, spin dry, the residue was purified by preparative TLC (dichloromethane: methanol 50: 1; petroleum ether: ethyl acetate 1: 1) to give Compound 13 (90mg, yield 22.3%).

Reference： [1]Patent: CN105481850,2016,A .Location in patent: Paragraph 0320; 0322; 0323; 0324

66
[ 1828-66-6 ]
C₁₈H₁₆NO₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
C₂₂H₂₆N₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100 mg		The present invention compound 41 reference from Example 32 to obtain compound E, then according to the following scheme prepared: To a 25mL round bottom flask was added DMF (3mL), in an ice bath with stirring was added sodium hydride (39mg, 1.61mmol), stirred for 5min, and then added portionwise compound E (300mg, 0.958mmol), stirred for 15min under ice bath, then at room temperature stirred for 1h, followed by morpholine-1-sulfonyl chloride F (356mg, 1.92mmol), the addition was completed, the reaction at room temperature overnight, the solvent was distilled off under reduced pressure, to give a paste G which was used directly in the next reaction. To a 100mL round bottom flask the crude G was dissolved in methanol (10 mL), stirred under an ice bath, portionwise added with sodium borohydride (121mg, 3.21 mmol), the addition was completed, the reaction at room temperature for 30min, the reaction solution was spin dry, the residue in water and ethyl acetate, the organic phase dried over anhydrous sodium sulfate, spin dry, the residue was purified by preparative TLC (dichloromethane: methanol 50: 1; petroleum ether: ethyl acetate 1: 1) to give Compound 41 (100mg, 24.3% yield).

Reference： [1]Patent: CN105481850,2016,A .Location in patent: Paragraph 0459; 0460; 0461; 0462; 0463

67
[ 1828-66-6 ]
[ 535170-20-8 ]
tert-butyl 2,6-difluoro-3-(morpholine-4-sulfonamido)phenylcarbamate [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 1632 - 1637

68
[ 1828-66-6 ]
C₂₄H₂₄FN₃O [ No CAS ]
C₂₈H₃₁FN₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With dmap; triethylamine; In dichloromethane; at 20℃; for 72h;	The solution of 86 (100 mg, 0.21 mmol), Et3N (0.03 mL, 0.21 mmol) and DMAP (122 mg, 0.41 mmol) in DCM (4 mL) was added <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (382 mg, 2.1 mmol), and the reaction mixture was stirred for 3d at rt. After completion, the mixture was purified by column (silica gel) to yield 88: 40 mg, 36% yield. 1H NMR (400 IVIFIz, Chloroform-d)8.22 (q, J = 5.2 Hz, 1H), 8.05 (s, 1H), 7.88 (s, 1H), 7.42 (q, J = 7.9 Hz, 1H), 7.36 - 7.18 (m,2H), 7.12 (td, J = 9.0, 4.5 Hz, 1H), 5.54 (d, J = 25.8 Hz, 1H), 4.05 - 3.84 (m, 2H), 3.72 (q, J =4.7 Hz, 4H), 3.53 (q, J = 5.7, 4.8 Hz, 2H), 3.24 (t, J = 4.7 Hz, 4H), 3.09 (d, J = 5.1 Hz, 3H),2.42 (s, 3H), 2.38 -2.19 (m, 2H), 2.01 (d, J = 6.0 Hz, 3H). LCMS (M+H): 539.55.

Reference： [1]Patent: WO2017/27768,2017,A1 .Location in patent: Page/Page column 67; 68

69
[ 1828-66-6 ]
N⁴-((3R,6S)-6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N²-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine [ No CAS ]
N-((3S,6R)-6-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.9%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of ~-((3R,6S)-6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N2 -(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine (200 mg, 0.57 mmol) in DCM (5 mL) wasadded triethylamine (115.1 mg, 1.14 mmol). The mixture was cooled to 0 C, and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (126.6 mg, 0.68 mmol) was added to the above mixture. The resulting mixturewas stirred at 0 oc for 30 min, then warm to room temperature and stirred overnight. The mixturewas concentrated in vacuo. The residue was purified by silica gel column chromatography((MeOH/DCM (v/v) = 1/40) to give the title compound as a yellow solid (71.1 mg, yield 24.9%).LC-MS (ESI, pos. ion) m/z: 501.9 [M+Ht;1H NMR (400 MHz, CDCb) 8 (ppm): 7.90 (s, IH), 7.59 (s, IH), 7.49 (s, IH), 6.95 (s, IH), 5.81(d, J = 6.9 Hz, IH), 5.42 (s, IH), 4.72-4.57 (m, 3H), 4.29-4.19 (m, IH), 4.08-3.91 (m, 3H), 3.86(s, 3H), 3.80-3.70 (m, 4H), 3.48 (t, J = 8.6 Hz, IH), 3.27-3.15 (m, 4H);13C NMR (100 MHz, CDCb) 8 (ppm): 158.1, 157.6, 153.4, 131.2, 122.9, 121.1, 104.4, 87.1, 81.0,73.6, 71.7, 66.1, 60.8, 53.9, 46.2, 39.2.
24.9%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of N4 - ((3R, 6S) -6-aminohexahydrofuro [3,2-b] furan-3-yl) -5-chloro-N2- (1-methyl- Yl) pyrimidine-2,4-diamine (200.0 mg, 0.57 mmol) in dichloromethane (5 mL) was added triethylamine (115.1 mg, 1.14 mmol).The reaction system was cooled to 0 C,Morpholine-4-sulfonyl chloride (126.6 mg, 0.68 mmol) was then added to the reaction system.The resulting reaction mixture was stirred at 0 C for 30 minutes,Then allowed to stand overnight at room temperature.After the reaction,Concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (MeOH / DCM (v / v) = 1/40)The title compound was obtained as a yellow solid (71.1 mg, yield 24.9%).

Reference： [1]Patent: WO2017/48675,2017,A1 .Location in patent: Paragraph 0409
[2]Patent: CN106478651,2017,A .Location in patent: Paragraph 0759; 0760; 0761; 0762; 0763; 0764

70
[ 1828-66-6 ]
N⁴-(6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N²-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine [ No CAS ]
N-(6-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.9%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of ~-(6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N2 -(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine (200 mg, 0.57 mmol) in DCM (5 mL) was added TEA(115.1 mg, 1.14 mmol). The mixture was cooled to 0 C, and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong>(126.6 mg, 0.68 mmol) was added to the above mixture. The resulting mixture was stirred at 0 ocfor 30 min, then warm to room temperature and stirred overnight. The mixture was concentratedin vacuo. The residue was purified by silica gel column chromatography ((MeOH/DCM (v/v) =1/40) to give the title compound as a yellow solid (71.1 mg, yield 24.9%).LC-MS (ESI, pos. ion) m/z: 501.9 [M+Ht;1H NMR (400 MHz, CDCb) 8 (ppm): 7.90 (s, 1H), 7.59 (s, 1H), 7.49 (s, 1H), 6.95 (s, 1H), 5.81(d, J = 6.9 Hz, 1H), 5.42 (s, 1H), 4.72-4.57 (m, 3H), 4.29-4.19 (m, 1H), 4.08-3.91 (m, 3H), 3.86(s, 3H), 3.80-3.70 (m, 4H), 3.48 (t, J = 8.6 Hz, 1H), 3.27-3.15 (m, 4H);13C NMR (100 MHz, CDCb) 8 (ppm): 158.1, 157.6, 153.4, 131.2, 122.9, 121.1, 104.4, 87.1, 81.0,73.6, 71.7, 66.1, 60.8, 53.9, 46.2, 39.2.
24.9%	With triethylamine; In dichloromethane; at 0 - 20℃;	To N4(6-aminohexahydrofuro [3,2-b] furan-3-yl) -5-chloro-N2- (1 -methyl-1H-pyrazol-Pyrimidine-2,4-diamine (200.0 mg, 0.57 mmol) in dichloromethane (5 mL) was added triethylamine (115.1 mg, 1.14 mmol).The reaction system was cooled to 0 C,Morpholine-4-sulfonyl chloride (126.6 mg, 0.68 mmol) was then added to the reaction system.The resulting reaction mixture was stirred at 0 C for 30 minutes,Then allowed to stand overnight at room temperature.After the reaction,Concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (MeOH / DCM (v / v) = 1/40)The title compound was obtained as a yellow solid (71.1 mg, yield 24.9%).

Reference： [1]Patent: WO2017/48675,2017,A1 .Location in patent: Paragraph 0408
[2]Patent: CN106478651,2017,A .Location in patent: Paragraph 0753; 0754; 0755; 0756; 0757; 0758

71
[ 1828-66-6 ]
[ 1342891-34-2 ]
N-((2,2-dimethyl-2H-chromen-6-yl)methyl)-N-phenylmorpholine-4-sulfonamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 992 - 1001

72
[ 1828-66-6 ]
[ 1391977-43-7 ]
N-cyclobutyl-N-((2,2-dimethyl-2H-chromen-6-yl)methyl)morpholine-4-sulfonamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 992 - 1001

73
[ 1828-66-6 ]
(S)-4-(3-hydroxy-4-methoxyphenyl)-3-methylene-1-(3,4,5-trimethoxyphenyl)azetidin-2-one [ No CAS ]
(S)-1-(3,4,5-trimethoxyphenyl)-4-(3-morpholinesulfonyloxy-4-methoxyphenyl)-3-methylenazetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; In dichloromethane; at 20℃; for 96h;	Compound 1 (20 mg, 0.054 mmol) was dissolved in 1.5 mL of dry DCM,To a stirred solution of TEA (14 mg, 0.162 mmol)4-morpholine sulfonyl chloride(15 mg, 0.081 mmol)After 4 d of reaction at room temperature, TLC (developing solvent:Petroleum ether / ethyl acetate = 1: 1) showed that the starting material 1 (Rf = 0.3) completely disappeared,(Rf = 0.25), stop the reaction (1 mL water quenching), add 10 mL of DCM, wash with water (2 x 10 mL), wash with saturated brine (10 mL), dry over anhydrous sodium sulfate for 3 h,The residue was collected by silica gel column chromatography, and the corresponding eluent was collected and evaporated to dryness to obtain 20 mg of white solid (29) in 71% yield

Reference： [1]Patent: CN107235883,2017,A .Location in patent: Paragraph 0161; 0162; 0163

74
[ 1828-66-6 ]
(R)-N-methyl-N-(5-azaspiro[2.4]heptan-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
(R)-N-methyl-N-(5-(morpholinosulfonyl)-5-azaspiro[2.4]heptan-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]

Reference： [1]MedChemComm,2018,vol. 9,p. 477 - 489

75
[ 1828-66-6 ]
(R)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine [ No CAS ]
(R)-N-methyl-N-(1-(morpholinosulfonyl)pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.2%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	General procedure: To an 93 (R)-N-methyl-N-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 5aa (70.0mg, 0.322mmol) solution in 1.00mL of 119 dichloromethane in a 5mL round-bottom flask, 151 methanesulfonyl chloride (36.9mg, 0.322mmol) and 121 N,N-diisopropylethylamine (0.0590mL, 0.339mmol) were added. Then, the reaction solution was stirred at room temperature overnight before being concentrated under reduced pressure. The residue was purified by flash column chromatography (methanol: dichloromethane=2:98).
Ca.40.2%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	10.0 mL of dichloromethane (CH2Cl2) was added to a 50-mL round-bottomed flask, which was then cooled down in an ice bath (low-temperature bath). After 0.300 mL of sulfuryl chloride (SO2Cl2) was added thereto, a solution of 213 mg of morpholine dissolved in 3.0 mL of dichloromethane (CH2Cl2) was slowly added while cooling in the ice bath (low-temperature bath). The reaction mixture was treated with 520 mg of trimethylamine and then stirred for about 2 hours. The resulting reaction product was dissolved with 20.0 mL of chloroform and then washed with 20.0 mL of ice water. The chloroform phase was separated, dried with magnesium sulfate (MgSO4), and then filtered. The resulting filtrate was distilled under reduced pressure. As a result, 160 mg of <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> was obtained with a yield of about 23.3%. 70.0 mg of (R)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 5-mL round-bottomed flask and then dissolved with 1.00 mL of dichloromethane (CH2Cl2). After 0.0390 mL of <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> was added thereto, the reaction mixture was treated with 0.0590 mL of N,N-diisopropylethylamine and then stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 47.0 mg of (R)-N-methyl-N-(1-(morpholinosulfonyl)pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 40.2%. 1H NMR (400 MHz, CDCl3) delta10.06 (s, 1H), 8.39 (s, 1H), 7.11-7.10 (m, 1H), 6.62-6.61 (m, 1H), 5.84-5.76 (m, 1H), 3.78-3.77 (m, 4H), 3.70-3.64 (m, 2H), 3.45-3.29 (m, 9H), 2.36-2.17 (m, 2H). LRMS (ESI) calcd for (C15H22N6O3S + H+) 367.2, found 367.1.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1495 - 1510
[2]Patent: EP3327021,2018,A1 .Location in patent: Paragraph 0211-0215

76
[ 1828-66-6 ]
{5-amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazol-4-yl}-(6-amino-5-methoxy-1H-indol-2-yl)methanone [ No CAS ]
N-[2-[5-amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazole-4-carbonyl]-5-methoxy-1H-indol-6-yl]morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47 mg	With pyridine; at 25℃; for 4h;	5-Amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazol-4-yl}-(6-amino-5-methoxy-1H-indol-2-yl)methanone (90 mg) was dissolved in pyridine (1.0 mL), and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (354 mg) was added. Then the mixture was stirred at 25C for four hours. The reaction solution was purified by Prep-HPLC to give the target compound (47 mg).

Reference： [1]Patent: EP3312172,2018,A1 .Location in patent: Paragraph 0488; 0490

77
[ 1828-66-6 ]
(5-amino-1-(4-(2-fluorophenoxy)-2-methylphenyl)-1H-pyrazol-4-yl)(6-amino-5-(difluoromethoxy)-1H-indol-2-yl)methanone hydrochloride [ No CAS ]
N-[2-[5-amino-1-[4-(2-fluorophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-5-(difluoromethoxy)-1H-indol-6-yl]morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27 mg	With pyridine; at 0 - 25℃; for 18h;	(5-Amino-1-(4-(2-fluorophenoxy)-2-methylphenyl)-1H-pyrazol-4-yl)(6-amino-5-(difluoromethoxy)-1H-indol-2-yl)methanone hydrochloride obtained in Step 4 (100 mg) and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (205 mg) were added to pyridine (0.91 mL) at 0C and the mixture was stirred at 25C for 18 hours. The reaction solution was diluted with ethyl acetate (5 mL) and then washed with 1 M hydrochloric acid (5 mL) and saturated saline (5 mL), and the organic layer was dried over magnesium sulfate. The drying agent was removed by filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane, 12% ? 100%) to give the target compound (27 mg).

Reference： [1]Patent: EP3312172,2018,A1 .Location in patent: Paragraph 0557; 0562

78
[ 1828-66-6 ]
(6-amino-5-fluoro-1H-indol-2-yl)-{5-amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazol-4-yl}methanone [ No CAS ]
N-[2-[5-amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazole-4-carbonyl]-5-fluoro-1H-indol-6-yl]morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58 mg	With pyridine; at 25℃; for 15h;	(6-Amino-5-fluoro-1H-indol-2-yl)-{5-amino-1-[6-(2-fluorophenoxy)-4-methylpyridin-3-yl]pyrazol-4-yl}methanone (70 mg) was dissolved in pyridine (1.2 mL), and <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> (230 mg) was added. Then the mixture was stirred at 25C for 15 hours. 0.1 M hydrochloric acid was added to the reaction solution and the mixture was extracted with ethyl acetate twice. The organic layers were washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The drying agent was removed by filtration, the filtrate was then concentrated under reduced pressure, and the resulting residue was purified by chromatography (hexane/ethyl acetate). The eluate containing the target compound was concentrated under reduced pressure and the resulting residue was crystallized from hexane/dichloromethane to give the target compound (58 mg).

Reference： [1]Patent: EP3312172,2018,A1 .Location in patent: Paragraph 0438; 0441

79
[ 1828-66-6 ]
C₄H₁₁N₃O₃S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 19156 - 19161

80
[ 1828-66-6 ]
[ 3963-78-8 ]
N-(3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 20℃; for 4h;	General procedure: Corresponding sulfonyl chloride (1.5 mmol)was added tothe solution of crude product 7 (255 mg,1 mmol) in dry pyridine(5 mL) and the mixture was stirred at room temperature for 4h.Then it was added to 10% aqueous HCl (50 mL) and the suspensionwasextracted with ethyl acetate. The organic phasewaswashed with brine, dried over anhydrous Na2SO4 and filtered.The residuewas purified by silica chromatography after removalof ethyl acetate to afford compounds 8a-v. 4.1.1.1. N-(3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methanesulfonamide (8a). Yellowsolid,

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 168,p. 45 - 57

81
[ 1828-66-6 ]
3,5-dimethyl-4-((2-(piperidin-4-ylamino)thieno[3,2-d]pyrimidin-4-yl)oxy)benzonitrile [ No CAS ]
C₂₄H₂₈N₆O₄S₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2019,vol. 93,p. 430 - 437

82
[ 292638-84-7 ]
[ 1828-66-6 ]
4-((2-chloro-2-phenylethyl)sulfonyl)morpholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4525 - 4533

83
[ 1828-66-6 ]
N-(4-(4-aminophenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-6-yl)cyclopropanecarboxamide [ No CAS ]
N-(4-(4-(morpholine-4-sulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)cyclopropanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A starting material, i.e., N(4-(4-aminophenyl)- 1 -tosyl- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide(100 mg) was stirred in 1 mL of pyridine. 1.5 equivalent of morpholine4- sulfonylchloride was inserted thereinto and stirred at 40C for 16 hours. Once the reaction was completed, d-HC1 was added to the said mixture, then an extraction using dichloromethane was performed, and then an organic layer was accordingly separated. After concentrating the mixture, the resulting concentrate was dissolved in MeOH/ THF (1:1) solution, and then 2N sodium hydroxide aqueous solution was added thereto and stirred at 30C for 12 hours. Once the reaction was completed, the said mixture was cooled down to room temperature, and saturated NH 4C1 aqueous solution was added thereto while being stirred. A produced solid was filtered out, and finally a product, i.e., N(4-(4-(morpholine-4- sulfonamido)phenyl)- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropane carboxamide was accordingly obtained.1H NMR (400 MHz, DMSO-d 6) oe 11.53 (s, 1H), 10.69 (s, 1H), 10.24 (s, 1H), 7.97(d, I = 5.7 Hz, 1H), 7.69 (d, I = 7.6 Hz, 2H), 7.47 (d, I = 8.2 Hz, 1H), 7.43 - 7.33 (m,3H), 7.11 (d, I = 7.8 Hz, 1H), 6.62- 6.51 (m, 1H), 3.63 - 3.50 (m, 5H), 3.18 - 3.06 (m,5H), 2.05 (d, I = 8.9 Hz, 1H), 0.88 - 0.77 (m, 4H)MS(ESI+) mlz 442 (M+H) +
		The starting material N-(4-(4-aminophenyl)-1-tosyl-1H-pyrrolo[2,3- b]pyridin- 6-yl)cyclopropanecarboxamide (4-(4-aminophenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-6- yl)cyclopropanecarboxamide) (100 mg) was stirred in pyridine (1 mL). 1.5 equivalents of <strong>[1828-66-6]morpholine-4-sulfonyl chloride</strong> was added thereto, and the mixture was stirred at 40 C for 16 hours. When the reaction was completed, the mixture was added with d-HCl, extracted with dichloromethane, and the organic layer was separated. After concentration of the mixture, it was dissolved in a MeOH/THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added, and the mixture was stirred at 30 C for 12 hours. When the reaction was complete, the mixture was cooled to room temperature and saturated aqueous NH4Cl solution was added with stirring. The resulting solid was filtered to give the product (N-(4-(4-(morpholine-4-sulfonamido)phenyl)-1H-pyrrolo[2,3- b]pyridin-6-yl)cyclopropanecarboxamide) was obtained.

Reference： [1]Patent: WO2019/78619,2019,A1 .Location in patent: Paragraph 1108; 1109; 1110; 1111; 1112
[2]Patent: KR2019/64555,2019,A .Location in patent: Paragraph 1310-1314

84
[ 1828-66-6 ]
C₁₄H₁₇FN₄ [ No CAS ]
N-((1-(6-fluoroquinazolin-4-yl)piperidin-3-yl)methyl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	General procedure: To a stirred solution of 1.1 (2.0 g, 9.33 mmol) in CH2C12 (25 mL) were added (0805) Et3N (1.8 g, 18.66 mmol) and methane sulphonyl chloride (1.60 g, 13.99 mmol) at RT. The reaction mixture was stirred ate RT for 16h. Upon complete consumption of starting material, the reaction mixture was poured into water (50 mL), extracted with CH2C12 (2 x 50 mL). The organic extracts were washed with saturated NaHC03 (40 mL), water (40 mL), brine (40 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 1.2 (2.0 g, crude) as a thick colorless liquid. MS (MM): m/z = 193.0 [M-Boc]+

Reference： [1]Patent: WO2019/89693,2019,A1 .Location in patent: Paragraph 00428

85
[ 1828-66-6 ]
2,3-dimethoxy-12-(2-(methylamino)ethyl)-[1,3]dioxolo[40,5':4,5]benzo[1,2-c]phenanthridin-13(12H)-one [ No CAS ]
N-(2-(2,3-dimethoxy-13-oxo-[1,3]dioxolo[40,5':4,5]benzo[1,2-c]phenan-thridin-12(13H)-yl)ethyl)-N-methylmorpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h;Reflux;	General procedure: To a solution of 12 (or 11, 0.24mmol) and DIPEA (2.4mmol) infreshly distilled dichloromethane (30 mL), the solution of acyl chlorides (0.32mmol) in dichloromethane (5 mL) was added slowlyat an ice bath. And then, the reaction solutionwas stirred and heatedunder reflux for 1 h (for 13-19, or at room temperature for 20-25).The reaction solution was cooled to room temperature. The solventwas evaporated under reduced pressure. The residue was purifiedby silica gel column chromatography to give target product.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 81 - 92

86
[ 1828-66-6 ]
12-(2-aminoethyl)-2,3-dimethoxy-[1,3]dioxolo[40,5':4,5]benzo[1,2-c]phenanthridin-13(12H)-one [ No CAS ]
N-(2-(2,3-dimethoxy-13-oxo-[1,3]dioxolo[40,5':4,5]benzo[1,2-c]phenanthridin-12(13H)-yl)ethyl)morpholine-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;	General procedure: To a solution of 12 (or 11, 0.24mmol) and DIPEA (2.4mmol) infreshly distilled dichloromethane (30 mL), the solution of acyl chlorides (0.32mmol) in dichloromethane (5 mL) was added slowlyat an ice bath. And then, the reaction solutionwas stirred and heatedunder reflux for 1 h (for 13-19, or at room temperature for 20-25).The reaction solution was cooled to room temperature. The solventwas evaporated under reduced pressure. The residue was purifiedby silica gel column chromatography to give target product.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 81 - 92

87
[ 1828-66-6 ]
N-(tert-butyl)quinolin-8-amine [ No CAS ]
N-(tert-butyl)-5-(morpholinosulfonyl)quinolin-8-amine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7564 - 7568

88
[ 1828-66-6 ]
[ 488720-99-6 ]
(R)-5-((S)-4,5-dimethoxy-1,3-dihydroisobenzofuran-1-yl)-4-methoxy-6-(morpholinosulfonyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline [ No CAS ]

Reference： [1]ChemMedChem,2019,vol. 14,p. 1968 - 1981

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Environmental hazards
Code	Phrase
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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

[ CAS No. 1828-66-6 ] {[proInfo.proName]}

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[ 1828-66-6 ] Synthesis Path-Upstream 1~6

[ 1828-66-6 ] Synthesis Path-Downstream 1~88

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Sulfonyl Chlorides

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