102153-63-9|6-Chloro-2-naphthylsulfonylchloride| Ambeed

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Quality Control of [ 102153-63-9 ] Purity: 95% SDS Specification

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Product Details of [ 102153-63-9 ]

CAS No. :	102153-63-9
Formula :	C₁₀H₆Cl₂O₂S
M.W :	261.12
SMILES Code :	ClC1=CC=C2C=C(C=CC2=C1)S(Cl)(=O)=O
MDL No. :	MFCD04037080
InChI Key :	IYFIYGSJZIICOZ-UHFFFAOYSA-N
Pubchem ID :	10635129

Safety of [ 102153-63-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Application In Synthesis of [ 102153-63-9 ]

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

Downstream synthetic route of [ 102153-63-9 ]

[ 102153-63-9 ] Synthesis Path-Downstream 1~35

1
[ 102153-63-9 ]
[ 57260-71-6 ]
1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; ethanol hydrochloride; ethyl acetate;	Referential Example 1 1-[(6-Chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride and trifluoroacetate In dichloromethane (20 ml), tert-butyl 1-piperazine carboxylate (856 mg) was dissolved. To the resulting solution, triethylamine (0.77 ml) and 6-chloro-2-naphthylsulfonylchloride (1.20 g) were added, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with 1N hydrochloric acid. The organic layer extracted was dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was dissolved in saturated ethanol hydrochloride (10 ml), followed by concentration under reduced pressure and washing with ethyl acetate, whereby the hydrochloride (1.62 g, quant.) of the title compound was obtained as a colorless solid. 1H-NMR (DMSO-d6) δ: 3.1-3.4(8H,m), 7.75(1H,dd,J=8.8,2.0 Hz), 7.86(1H,dd,J=8.8,1.5 Hz), 8.22(1H,d,J=8.8 Hz), 8.26-8.32(2H,m), 8.56(1H,s), 8.63(2H,br s). MS (FAB) m/z: 311 [(M+H)+, Cl35], 313 [(M+H)+, Cl37].

References: [1]Patent: US6525042,2003,B1 .

2
N-{5-[(3S)-3-amino-2-oxo-1-pyrrolidinyl]-2,3-dihydro-1H-inden-1-yl}-2,2,2-trifluoroacetamide hydrochloride [ No CAS ]
[ 102153-63-9 ]
[ 879500-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; for 19.5h;	A suspension of /v-{5-[(3S)-3-amino-2-oxo-1-pyrrolidinyl]-2,3-dihydro-1/-/-inden-1-yl}-2,2,2-trifluoroacetamide hydrochloride (Intermediate 22) (145mg) in anhydrous MeCN (20ml) was cooled in an ice bath and treated with N,N-diisopropylethyl amine (69.4ul) and pyridine (96.8 ul). 6-Chloro-2-naphthalenesulfonyl chloride (125 mg) was added in a single portion and the suspension was stirred in the ice bath for 30min. The cooling bath was removed and reaction mixture was stirred at room temperature for 1h, diluted with anhydrous MeCN (10ml) and stirred at room temperature for 18h. The thick suspension was evaporated to dryness and partitioned between DCM (2 x 50ml) and saturated aqueous sodium hydrogen carbonate solution (30ml). The organic extracts were combined, washed with brine, passed through a hydrophobic frit and evaporated to a yellow solid. Purification on 20g silica SPE column eluting with [50:1] DCM:MeOH gave asticky orange solid. This solid was triturated with diethyl ether and the title compound collected by filtration (155mg). Mass spectrum: Found : MH+ 552 H.p.l.c. Rt 3.51min

References: [1]Patent: WO2006/27186,2006,A1 .Location in patent: Page/Page column 39-40.

3
[ 102153-63-9 ]
[ 134749-45-4 ]
[ 229647-15-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1237 - 1244.

4
[ 102153-63-9 ]
[ 229647-14-7 ]
4-(6-chloronaphthalen-2-ylsulfonyl)-1-[1-(pyridin-4-yl)piperidin-4-ylmethyl]piperazin-2-one [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1237 - 1244.

5
[ 102153-63-9 ]
4-[[1-(4-pyridinyl)-4-piperidinyl]methyl]piperazine mono(trifluoroacetate) [ No CAS ]
4-(6-chloronaphthalen-2-ylsulfonyl)-1-[1-(pyridin-4-yl)piperidin-4-ylmethyl]piperazine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 1237 - 1244.

6
[ 102153-63-9 ]
[ 74141-19-8 ]
[ 318987-05-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2002,vol. 50,p. 1187 - 1194.

7
[ 102153-63-9 ]
[ 229647-17-0 ]
[ 229646-51-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,2002,vol. 50,p. 1187 - 1194.

8
[ 102878-14-8 ]
[ 102153-63-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2935 - 2939.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 5167 - 5182.
[3]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 2243 - 2260.

9
[ 102153-63-9 ]
[ 57260-71-6 ]
[ 216866-88-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With triethylamine; In dichloromethane; for 2h;	To a stirring solution of N-Boc-piperazine (400 mg, 2.1 mmol) and triethylamine (1 mL, 7 mml) in methylene chloride (5 mL) was added <strong>[102153-63-9]6-chloro-2-naphthalenesulfonyl chloride</strong> (500 mg, 1.9 mmol). After 2 h the solution was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed on a (Biotage) silica column eluting with ethyl acetate:hexanes (2:8) to give 300 mg (38%). 1H-NMR (CDCl3): δ (s, 9H, 1.4), (m, 4H, 3.07), (m, 4H, 3.55), (dd, 1H, 7.55, J=1,12), (dd, 1H, 7.75, J=1,12), (m, 4H, 7.9), (s, 1H, 8.3), MS (FD) 410.1 M+; IR (chloroform) carbonyl 1691 cm-1. Anal. Calcd: C, 55.54; H, 5.64; N, 6.82; Cl, 8.63; Found: C, 55.71; H, 5.76; N, 6.85; Cl, 8.76.
300 mg (38%)	With triethylamine; In dichloromethane;	C. 1-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine To a stirring solution of N-Boc-piperazine (400 mg, 2.1 mmol) and triethylamine (1 mL, 7 mmol) in methylene chloride (5 mL) was added <strong>[102153-63-9]6-chloro-2-naphthalenesulfonyl chloride</strong> (500 mg, 1.9 mmol). After 2 h the solution was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed on a (Biotage) silica column, eluding with ethyl acetate:hexanes (2:8), to give 300 mg (38%). 1H-NMR (CDCl3): δ(s, 9H, 1.4), (m, 4H, 3.07), (m, 4H, 3.55), (dd, 1H, 7.55, J=1,12), (dd, 1H, 7.75, J=1,12), (m, 4H, 7.9), (s, 1H, 8.3), FD-MS, m/e 410.1 (M+); IR (chloroform) carbonyl 1691 cm-1.

References: [1]Patent: US6660739,2003,B1 .Location in patent: Page column 18.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2935 - 2939.
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 5167 - 5182.
[4]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954.
[5]Patent: US2004/97491,2004,A1 .
[6]Patent: US6359134,2002,B1 .Location in patent: Referential example 3.

10
[ 102153-63-9 ]
[ 623-33-6 ]
[ 318986-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triethylamine; In hexane; dichloromethane;	Synthesis of ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)amino]acetate Glycine ethyl ester hydrochloride (9.88 g) was suspended in methylene chloride (500 ml), and triethylamine (20.2 ml) and then 6-chloronaphthalene-2-sulfonyl chloride (17.6 g) were added to the suspension under cooling with ice. After stirring at room temperature for 1 hour and adjusting the mixture to pH 2 by addition of 1N hydrochloric acid, the mixture was extracted with methylene chloride. The methylene chloride layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After washing the resulting crystals in n-hexane, the crystals were collected by filtration and air-dried to obtain the title compound (22.4 g). NMR spectrum (*CDCl3) δppm: 8.43-8.40(1H,m), 7.95-7.87(4H,m), 7.57(1H,dd,J=2,9 Hz), 5.22-5.15(1H,m), 4.01(2H,q,J=7 Hz), 3.82(2H,d,J=6 Hz), 1.11(3H,t,J=7 Hz)

References: [1]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 406 - 412.
[2]Patent: US2003/45520,2003,A1 .

11
[ 102153-63-9 ]
N-(tert-butyloxycarbonyl)-1,2-ethanediamine hydrochloride [ No CAS ]
[ 705302-70-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 459 - 462.

12
[ 102153-63-9 ]
ethyl (R)-3-amino-2-(benzyloxycarbonylamino)propionate hydrochloride [ No CAS ]
[ 705302-73-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 459 - 462.

13
[ 102153-63-9 ]
[ 56-40-6 ]
[ 123090-06-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 459 - 462.

14
[ 222986-36-9 ]
[ 102153-63-9 ]
[ 207798-71-8 ]