132898-96-5|2,3-Dioxoindoline-5-sulfonyl chloride| Ambeed

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Quality Control of [ 132898-96-5 ] Purity: 91% SDS Specification

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Product Details of [ 132898-96-5 ]

CAS No. :	132898-96-5
Formula :	C₈H₄ClNO₄S
M.W :	245.64
SMILES Code :	O=S(C1=CC2=C(NC(C2=O)=O)C=C1)(Cl)=O
MDL No. :	MFCD11974220
InChI Key :	JUJRKHHCIXKFQG-UHFFFAOYSA-N
Pubchem ID :	15908947

Safety of [ 132898-96-5 ]

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 [ 132898-96-5 ]

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

Downstream synthetic route of [ 132898-96-5 ]

[ 132898-96-5 ] Synthesis Path-Downstream 1~35

1
[ 503-29-7 ]
[ 132898-96-5 ]
5-(azetidin-1-ylsulfonyl)indoline-2,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2188 - 2191.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

2
[ 123-75-1 ]
[ 132898-96-5 ]
[ 220510-17-8 ]

Yield	Reaction Conditions	Operation in experiment
39%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0℃; for 2h;	Step 1: 5-(Pyrrolidin-1-ylsulfonyl)-1H-indole-2,3-dione To a cold solution of <strong>[132898-96-5]2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride</strong> (2.00 g, 8.14 mmol) in a 1:1 mixture of THF: CHCl3 (96 mL) was added drop-wise via syringe pump over a period of 1 hr a solution of pyrrolidine (0.885 mL, 10.6 mmol) and N, N-diisopropylethyl amine (2.84 mL, 16.3 mmol, 2 eq) in chloroform (16 mL) under a dry N2 atmosphere with cooling in an ice bath. After stirring for 1 h., the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 80/20 CH2Cl2/EtOAc to give the title compound as a greenish-yellow solid (0.88 g, 39% yield). NMR (300 Mz, DMSO-d6): consistent. MS: (ES-) m/z 279 [M-H].

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2188 - 2191.
[2]Patent: US2005/250798,2005,A1 .Location in patent: Page/Page column 36.
[3]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

3
[ 110-89-4 ]
[ 132898-96-5 ]
5-[(piperidin-1-yl)sulfonyl]-1H-indole-2,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2188 - 2191.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

4
[ 111-49-9 ]
[ 132898-96-5 ]
5-(azepane-1-sulfonyl)-1<i>H</i>-indole-2,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

5
[ 29802-22-0 ]
[ 132898-96-5 ]
(S)-5-{1-[[2-(dimethylamino)carbonyl]pyrrolidinyl]sulfonyl}isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

6
[ 64030-44-0 ]
[ 132898-96-5 ]
(S)-5-{1-[2-(anilinomethyl)pyrrolidnyl]sulfonyl}isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

7
[ 68295-45-4 ]
[ 132898-96-5 ]
(R)-5-{1-[2-(anilinomethyl)pyrrolidinyl]sulfonyl}isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

8
[ 2812-46-6 ]
[ 132898-96-5 ]
(S)-5-{1-[(2-tert-butoxycarbonyl)pyrrolidinyl}sulfonyl]isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

9
[ 38256-93-8 ]
[ 132898-96-5 ]
2,3-dioxo-2,3-dihydro-1<i>H</i>-indole-5-sulfonic acid (2-methoxy-ethyl)-methyl-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

10
[ 63126-47-6 ]
[ 132898-96-5 ]
[ 220509-74-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0℃; for 1.5h;	Step 2: 5-[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold suspension of <strong>[132898-96-5]2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride</strong> (5.28 g, 21.5 mmol) in a 1:1 mixture of THF:CHCl3 (254 mL) was added drop-wise via syringe pump a solution of (S)-(+)-2-(methoxymethyl)-pyrrolidine (3.45 mL, 28.0 mmol, 1.3 eq) (Aldrich) and N,N-diisopropylethylamine (7.49 mL, 43 mmol, 2 eq) in CHCl3 (42 mL) over a period of 70 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring an additional 20 minutes the mixture was concentrated. The residue was flash chromatographed (Biotage KP silica gel, 98/2 CH2Cl2/CH3OH) to give the title compound as a dark greenish-yellow foam (6.48 g. 93% yield). NMR (400 MHz, DMSO-d6): consistent MS: (API-ES-) m/z 323[M-H].

References: [1]Patent: US2005/250798,2005,A1 .Location in patent: Page/Page column 21.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 6704 - 6715.
[4]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7755 - 7768.

11
[ 2133-40-6 ]
[ 132898-96-5 ]
(S)-5-{1-[(2-methoxycarbonyl)pyrrolidinyl]sulfonyl}isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

12
[ 63126-47-6 ]
[ 132898-96-5 ]
[ 220509-85-3 ]

Yield	Reaction Conditions	Operation in experiment
63.8%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0℃; for 2.5h;	Step 1: 5-[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a stirred cold suspension of 2,3-dioxo-2,3-dihydro-1H-indol-5-sulfonyl chloride (5.00 g, 20.4 mmol) in a 1:1 mixture of THF: CHCl3 (140 mL) was added dropwise, via syringe pump, a solution of N,N-diisopropylethylamine (7.11 mL, 40.8 mmol, 2 eq) and (R)-2-(Methoxymethyl)pyrrolidine (3.27 mL, 26.5 mmol, 1.3 eq) in CHCl3 (60 mL) over a period of 1.5 hours with cooling in an ice bath. After stirring an additional 1 h, the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 95/5 CH2Cl2/CH3OH followed by a second chromatography on silica gel eluding with EtOAc to give 4.21 g (63.8%) of the title compound. NMR (400 MHz, DMSO-d6): consistent.

References: [1]Patent: US2005/250798,2005,A1 .Location in patent: Page/Page column 28.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

13
[ 132898-96-5 ]
[ 106865-52-5 ]
(S)-5-{1-[2-(thiophenoxymethyl)pyrrolidinyl]sulfonyl}isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

14
[ 132898-96-5 ]
[ 174213-76-4 ]
[ 220509-98-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0 - 20℃; for 64.83h;	Step 1: 5-[(2S)-2-(Phenoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold solution of 2,3-dioxo-2,3-dihydro-1-H-indole-5-sulfonylchloride (3.80 g, 15.5 mmol) in a 1:1 mixture of THF:CHCl3 (194 mL) was added drop-wise via syringe pump a solution of (2S)-2-(phenoxymethyl)pyrrolidine (2.85 g, 16.1 mmol, 1.03 eq) (J. Med. Chem, 44, 2014, 2001) and N,N-diisopropylethylamine (5.61 mL, 32.2 mmol, 2 eq) in CHCl3 (30 mL) over a period of 50 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring at room temperature for 64 hr the reaction mixture was concentrated and the crude product was flash chromatographed twice using Biotage KP silica gel, and gradient of 98/2 CH2Cl2/CH3OH as eluent on the first column and 90/10 CH2Cl2/CH3OH as eluent on the second column to give the title compound as a dark green solid (5.29 g, 88% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (ES-) m/z 385 [M-H]. MS: (ES+) m/z 387 [M+H].

References: [1]Patent: US2005/250798,2005,A1 .Location in patent: Page/Page column 23.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5041 - 5046.
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 6704 - 6715.
[6]Journal of Medicinal Chemistry,2008,vol. 51,p. 8057 - 8067.
[7]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7755 - 7768.

15
[ 132898-96-5 ]
[ 25746-83-2 ]
(S)-5-{1-[2-(phenylaminocarbonyl)pyrrolidinyl}sulfonyl]isatin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.

16
[ 80789-74-8 ]
[ 132898-96-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With trichlorophosphate; In sulfolane; at 60℃; for 3h;	(16) Phosphorus oxychloride (13.2 mL, 141.6 mmol) was added to a solution of 5-isatinsulfonic acid (5), sodium salt hydrate (8.0 g, 30.0 mmol) in tetramethylene sulfone (40 mL). The mixture was heated to 60 C. for 3 h, then cooled to 0 C. The reaction mixture was poured into 150 g of ice. The solid was filtered out and washed with cold water, then the solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. The ethyl acetate was evaporated in reduced pressure to afford 6.12 g (83%) of 6 as a pale yellow solid, mp 188.2-190.1 C. 1H NMR (300 MHz, DMSO) delta 11.1 (s, 1H), 7.82 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 7.60 (s, 1H), 6.89 (d, J=8.1 Hz, 1H).
82%	With trichlorophosphate; at 60℃; for 3h;	A suspension of sodium 2,3-dioxoindoline-5-sulfonate dihydrate (5.0 g, 17.53 mmol) and POCl3 (8.17 ml, 88 mmol) in sulfolane (25 ml, 264 mmol) was heated at 60 C. for 3 hours. The solution was cooled to 0 C. and water (60 ml) was added drop wise; the green precipitate was filtered and washed with a small amount of water. The solid was dissolved in ethyl acetate and washed three times with water; the organic phase was then dried over sodium sulfate and evaporated to give a crude solid that was purified by crystallization from hexane/ethyl acetate 1:1 to give 2,3-dioxoindoline-5-sulfonyl chloride (3.52 g, 14.33 mmol, 82% yield).
82%	With trichlorophosphate; In sulfolane; at 60℃; for 3h;	Example 27 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy) phenyl)-2-(2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1 -yl)acetoxy)- ethyl)pyridine 1 -oxide (compound 151 ) Scheme 27 Step 1 : Preparation of 2,3-dioxoindoline-5-sulfonyl chloride (147) A suspension of sodium 2,3-dioxoindoline-5-sulfonate dihydrate (5.0 g, 17.53 mmol) and POCI3 (8.17 ml, 88 mmol) in sulfolane (25 ml, 264 mmol) was heated at 60C for 3 hours. The solution was cooled to 0C and water (60 ml) was added drop wise; the green precipitate was filtered and washed with a small amount of water. The solid was dissolved in ethyl acetate and washed three times with water; the organic phase was then dried over sodium sulfate and evaporated to give a crude solid that was purified by crystallization from hexane/ethyl acetate 1 : 1 to give 2,3-dioxoindoline-5-sulfonyl chloride (3.52 g, 14.33 mmol, 82% yield).

68%	With trichlorophosphate; In sulfolane; at 60℃; for 3h;	Phosphorus oxychloride (27.17 g, 177.2 mmol) was added to a mixture of 5- isatinsulfonic acid sodium salt dihydrate (10.1 g, 35.5 mmol) in of tetramethylene sulfone (50 ml). The resulting mixture was stirred at 60 0C for 3 h. After cooling to 0 0C, water (120 ml) was added. The green precipitate was filtered, dissolved in ethyl acetate (200 ml) and washed with water (150 ml). The organic extracts were collected, dried over Na2SO4, filtered and the solvent removed under reduced pressure to provide a green solid. The pure compound rpm 121 was obtained after recrystallization from ethyl acetate/hexane 1 : 1 as yellow solid (5.9 g, 21.1 mmol, 68 %). 1H NMR (400 MHz, CDC13:CD3CN 1 :1) delta 7.22 (IH, d, J 8.4 Hz), 8.16 (IH, d, J2.0 Hz), 8.23 (IH, dd, / 8.4, 2.0 Hz), 9.47 (IH, s), mp 200- 202 0C.
66%	With trichlorophosphate; In sulfolane; at 60℃; for 3h;	Step 1: 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride A mixture of isatinsulfonic acid sodium salt hydrate (10.00 g, 39.7 mmol) and phosphorous oxychloride (18.5 mL, 199 mmol, 5 eq) in tetramethylene sulfone (50 mL) was heated at 60 C. for 3 hours under a dry N2 atmosphere. The reaction was cooled in an ice bath to 0 C. and water was cautiously added drop-wise, keeping the internal temperature below 6 C. The resulting green solid was collected by filtration and was washed well with water. The solid was dissolved in ethyl acetate (200 mL) and washed again with water (3*50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude product in 85% yield. The solid was recrystallized from ethyl acetate: hexanes with hot filtration to give the title compound (5.81 g, 66% yield). NMR (400 MHz, DMSO-d6): consistent.

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.
[2]Patent: US2009/68105,2009,A1 .Location in patent: Page/Page column 9.
[3]Patent: US2013/102576,2013,A1 .Location in patent: Paragraph 0510.
[4]Patent: WO2013/57013,2013,A2 .Location in patent: Page/Page column 130.
[5]MedChemComm,2016,vol. 7,p. 1628 - 1639.
[6]Patent: WO2007/117699,2007,A2 .Location in patent: Page/Page column 26.
[7]Journal of Medicinal Chemistry,2006,vol. 49,p. 6704 - 6715.
[8]Patent: US2005/250798,2005,A1 .Location in patent: Page/Page column 21.
[9]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7755 - 7768.
[10]Journal of Medicinal Chemistry,2001,vol. 44,p. 2015 - 2026.
[11]Journal of Medicinal Chemistry,2016,vol. 59,p. 419 - 430.

17
[ 1033717-72-4 ]
[ 132898-96-5 ]
5-(2-(pyridin-4-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

18
[ 132898-96-5 ]
[ 161416-57-5 ]
[ 872254-12-1 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

19
[ 132898-96-5 ]
[ 182323-92-8 ]
[ 872254-10-9 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

20
[ 132898-96-5 ]
[ 124-40-3 ]
[ 144405-95-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 2.5h;Inert atmosphere;	To a mixture of <strong>[132898-96-5]2,3-dioxoindoline-5-sulfonyl chloride</strong> (0.800 g, 3.26 mmol) in dry THF (10 ml), cooled at 0 C. under nitrogen, DIPEA (1.138 ml, 6.51 mmol) and dimethylamine 2M in THF (2.117 ml, 4.23 mmol) were added, and the mixture was allowed to stir at room temperature for 2.5 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give N,N-dimethyl-2,3-dioxoindoline-5-sulfonamide (0.639 g, 2.51 mmol, 77% yield). MS/ESI+ 254.9 [MH]+.
77%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 2.5h;Inert atmosphere;	Step 2: Preparation of N, N-dimethyl-2,3-dioxoindoline-5-sulfonamide (148) To a mixture of <strong>[132898-96-5]2,3-dioxoindoline-5-sulfonyl chloride</strong> (0.800 g, 3.26 mmol) in dry THF (10 ml), cooled at 0C under nitrogen, DI PEA (1 .138 ml, 6.51 mmol) and dimethylamine 2M in TH F (2.1 17 ml, 4.23 mmol) were added and the mixture was allowed to stir at room temperature for 2.5 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give N ,N-dimethyl-2,3-dioxoindoline-5-sulfonamide (0.639 g, 2.51 mmol, 77% yield). MS/ESI+ 254.9 [MH] +.
68%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;	A mixture of dimethylamine (2M solution in THF) (0.668 mmol, 1.3 eq) and DIPEA (0.139 g, 1.02 mmol, 2 eq) was added to a solution of rpm 121 (0.126 g, 0.514 mmol) in anhydrous THF (4 ml) at 0 0C under Ar. The reaction mixture was stirred overnight at room temperature, and the mixture was poured into water (5 ml). The product was extracted with ethyl acetate (3 x 10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent removed under reduced pressure. The pure compound rpm 123 was obtained after trituration with ethyl acetate (5 ml) as a yellow solid (0.90 g, 0.354 mmol, 68%), mp 150- <n="28"/>152 0C (lit mp 233 0C.) 1H NMR (400 MHz, DMSO-d6) delta 2.60 (6H, s), 7.09 (IH, d, J 8.3 Hz), 7.68 (IH, d, J2.0 Hz), 7.91 (IH, dd, J 8.3, 2.0 Hz), 1 1.44 (IH, s).

References: [1]Patent: US2013/102576,2013,A1 .Location in patent: Paragraph 0511.
[2]Patent: WO2013/57013,2013,A2 .Location in patent: Page/Page column 130; 131.
[3]Patent: WO2007/117699,2007,A2 .Location in patent: Page/Page column 26-27.

21
[ 110-91-8 ]
[ 132898-96-5 ]
[ 220510-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at -50 - 20℃;	Morpholine (1.1 mL, 12.2 mmol) was added to a solution of 2,3-diupsilonxoLndoline-5-sulfonyl chloride (3.0 g, 12.2 mmol) and diibopropylethyl amine (7,0 mL, 40 mmol) m 1 :1 CH2CWTHF ( 120 mL at -50 C. The solution was warmed to room temperature and stirred at that temperature for 12 hours. The reaction mixture was concentrated, then dissolved m CHjCl2. and washed with saturated NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, then concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH:CU) to provide 2.4 g of the product
	In dichloromethane; chloroform; at 20℃; for 3h;	A solution of rpml21 (0.211 g, 0.861 mmol) and morpholine (0.187 g, 2.139 mmol, 2.5 eq), in anhydrous DCM (7 ml) and anhydrous chloroform (1 ml) was stirred for 3h at room temperature under Ar. The yellow precipitate was collected by filtration and dried under vacuum. The crude product was used in the next step without further purification.

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2188 - 2191.
[2]Patent: WO2010/77839,2010,A1 .Location in patent: Page/Page column 121.
[3]Patent: WO2007/117699,2007,A2 .Location in patent: Page/Page column 33.

22
[ 132898-96-5 ]
[ 174213-51-5 ]
[ 220509-98-8 ]

Yield	Reaction Conditions	Operation in experiment
84%		Example 4 (S)-5-(2-Phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (10). To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0 C. The mixture was stirred at 0 C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0 C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9 C. 1H NMR (300 MHz, CDCl3) delta 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

References: [1]Patent: US2009/68105,2009,A1 .Location in patent: Page/Page column 10.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

23
[ 132898-96-5 ]
[ 161417-33-0 ]
[ 872254-12-1 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

24
[ 132898-96-5 ]
[ 872254-31-4 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

25
[ 132898-96-5 ]
[ 872254-32-5 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

26
[ 132898-96-5 ]
[ 872254-19-8 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6704 - 6715.
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 7637 - 7647.

27
[ 132898-96-5 ]
[ 899818-48-5 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

28
[ 132898-96-5 ]
[ 946609-26-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

29
[ 132898-96-5 ]
[ 946609-16-1 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

30
[ 132898-96-5 ]
[ 946609-17-2 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

31
[ 132898-96-5 ]
2-[1-methyl-2-oxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1,2-dihydro-indol-3-ylidene]-malononitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

32
[ 132898-96-5 ]
2-[1-benzyl-2-oxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1,2-dihydroindol-3-ylidene]-malononitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

33
[ 132898-96-5 ]
2-[1-(4-hydroxy-benzyl)-2-oxo-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1,2-dihydro-indol-3-ylidene]-malononitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

34
[ 132898-96-5 ]
[ 946609-21-8 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

35
[ 132898-96-5 ]
2-{1-benzyl-2-oxo-5-[2-(pyridine-3-yloxymethyl)-pyrrolidine-1-sulfonyl]-1,2-dihydro-indol-3-ylidene}-malononitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3751 - 3755.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 132898-96-5

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CAS No.: 132898-96-5

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Product Details of [ 132898-96-5 ]

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Application In Synthesis of [ 132898-96-5 ]

[ 132898-96-5 ] Synthesis Path-Downstream 1~35

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Historical Records

Technical Information

Categories

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

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