[ CAS No. 1133819-87-0 ] {[proInfo.proName]}

Name: 1133819-87-0|5-(4-(2-(3-Methoxyphenyl)-2-oxoethoxy)benzyl)thiazolidine-2,4-dione|98+%
Brand: Ambeed
SKU: A360389
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Quality Control of [ 1133819-87-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1133819-87-0 ]

CAS No. :	1133819-87-0	MDL No. :	MFCD28502493
Formula :	C₁₉H₁₇NO₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YAUMOGALQJYOJQ-UHFFFAOYSA-N
M.W :	371.41	Pubchem ID :	25230266
Synonyms :	MSDC-0602	Chemical Name :	5-(4-(2-(3-Methoxyphenyl)-2-oxoethoxy)benzyl)thiazolidine-2,4-dione

Safety of [ 1133819-87-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1133819-87-0 ]

* 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 [ 1133819-87-0 ]

[ 1133819-87-0 ] Synthesis Path-Downstream 1~18

1
[ 1133820-10-6 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 5h; Reflux;	16 6.16. 5-[[4-[2-(4-Methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-2,4-thiazolidinedione 7 To a solution of 5-[[4-[2-(4-methoxyphenyl)-2-hydroxyethoxy]phenyl]methyl]-2,4-thiazolidinedione 24b (2.82 g, 7.55 mmol) in EtOAc (25 mL) was added 2-iodoxybenoic acid (1.23 g, 4.4 mmol). The mixture was heated to reflux for 5 h at which point it was judged (HPLC) to be ca. 50% complete and an additional 1.50 g (5.35 mmol) of IBX was added. After an additional 5 h at reflux, HPLC analysis indicated that the reaction was complete and the mixture was cooled to room temperature and filtered through a small pad of silica and the pad was rinsed with EtOAc. The solvent was removed in vacuo and the residue was purified by chromatography on a column of silica gel using the flash technique (40 mm OD, 100 g, 230-400 mesh), eluting with 0-15% EtOAc-CH2Cl2. Fractions containing 7 were pooled to give 7 (2.15 g, 77%) as a pale tan solid. 1H NMR (400 MHz, DMSO-d6): δ = 12.03 (s, 1), 7.62 (d, J = 7.7 Hz, 1), 7.45-7.51 (2), 7.26 (m, 1), 7.16 (d, J = 8.6 Hz, 2), 6.91 (d, J = 8.6 Hz, 2), 5.55 (s, 2), 4.88 (m, 1), 3.84 (s, 3), 3.31 (dd, J = 14.2, 4.2 Hz, 1), 3.05 (dd, J = 14.2, 9.2 Hz, 1); MS (ESI+) m/z 394.3 (M+Na); MS (ESI-) m/z 370.3 (M-H); Anal. Calcd. For C19H17NO5S C, 61.44; H, 4.61; N, 3.77. Found: C, 61.29; H, 4.52; N, 3.57.
54%	With phosphorus pentoxide; dimethyl sulfoxide; triethylamine In dichloromethane at 0 - 20℃; for 2h;	5.5 Step 5: Preparation of 5-{4-[2-(3-methoxyphenyl)-2-oxoetb.oxy]benzyl}-l,3- thiazolidine-2,4-dione; [00162] To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-l,3- thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 ml) was added DMSO (0.5 ml) and the solution was cooled to 0°C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.33g (54%) of the title compound as a white solid. MS (ESI+) for Ci9H17NO5S m/z 372.0 (M+H)+. MS (ESI-) for Ci9Hi7NO5S m/z 370.1 (M-H)".
54%	With phosphorus pentoxide; dimethyl sulfoxide; triethylamine In dichloromethane at 0 - 20℃;	5.5 To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-1,3- thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0 °C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.33 g (54%) of the title compound as a white solid. MS (ESI+) for C19Hi7NO5S m/z 372.0 (M+H)+. MS (ESI-) for C19H17NO5S m/z 370.1 (M-H)

54%	With phosphorus pentoxide; dimethyl sulfoxide; triethylamine In dichloromethane at 0 - 20℃; for 2h;	5.5 Step 5: Preparation of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyI}-l,3- thiazolidine-2,4-dione. To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-l ,3- thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0 °C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.33 g (54%) of the title compound as a white solid. MS (ESI+) for Ci9H17N05S m/z 372.0 (M+H)+. MS (ESI-) for C19H,7N05S m z 370.1 (M-H)".
54%	With phosphorus pentoxide; dimethyl sulfoxide; triethylamine In dichloromethane at 0 - 20℃; for 2h;	5.5 Step 5: Preparation of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0° C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.33 g (54%) of the title compound as a white solid. MS (ESI+) for C19H17NO5S m/z 372.0 (M+H)+. MS (ESI-) for C19H17NO5S m/z 370.1 (M-H)-.

Reference： [1]Tanis, Steven P.; Colca, Jerry R.; Parker, Timothy T.; Artman, Gerald D.; Larsen, Scott D.; McDonald, William G.; Gadwood, Robert C.; Kletzien, Rolf F.; Zeller, James B.; Lee, Pil H.; Adams, Wade J. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5870 - 5884]
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2009/38681, 2009, A1 Location in patent: Page/Page column 40
[3]Current Patent Assignee: METABOLIC SOLUTIONS DEVELOPMENT COMAPNY, LLC - WO2010/105048, 2010, A1 Location in patent: Page/Page column 63-64
[4]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2014/93114, 2014, A1 Location in patent: Paragraph 0399; 0400
[5]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2 Location in patent: Page/Page column 109

2
[ 5000-65-7 ]
[ 74772-78-4 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-(4-hydroxybenzyl)-2,4-thiazolidinedione With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 2-bromo-3'-methoxyacetophenone In dimethyl sulfoxide for 2h;	1 [0139] Example 1: Preparation of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-l,3- thiazolidine-2,4-dione [0140] To a stirring solution of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (100 mg, 0.4 mmol) in DMSO (2ml), potassium tert-butoxide (106 mg, 0.941 mmol) was added. Stirring continued at RT for about 1 hour. 2-Bromo-3'-methoxyacetophenone (100 mg, 0.5 mmol) was then added to the mixture. After 2 hours, LCMS showed that the reaction was complete. The reaction mixture was partitioned between EtOAc and water, and the aqueous phase was extracted with EtOAc. Combined extracts were washed with brine, dried on (Na2S04), filtered, and evaporated in vacuo. The residue was analyzed on a small RediSep column eluting with 0-10% acetone/DCM. Fractions containing the product were combined and evaporated in vacuo to afford 70mg of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-l,3- thiazolidine-2,4-dione as a pale yellow solid.

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2011/133442, 2011, A1 Location in patent: Page/Page column 33-34

3
[ 5000-65-7 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 1 h / 20 °C 1.2: 2 h 2.1: hydroxylamine hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 20 °C 3.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / water; tetrahydrofuran / 0.17 h / 20 °C 3.2: 20 °C 3.3: pH 6 - 7 4.1: hydrogenchloride; water / Reflux
	Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 12 h / 20 °C / Inert atmosphere 2: piperidine / ethanol / 12 h / Reflux; Inert atmosphere 3: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2012/21476, 2012, A1
[2]Tanis, Steven P.; Colca, Jerry R.; Parker, Timothy T.; Artman, Gerald D.; Larsen, Scott D.; McDonald, William G.; Gadwood, Robert C.; Kletzien, Rolf F.; Zeller, James B.; Lee, Pil H.; Adams, Wade J. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5870 - 5884]

4
[ 103788-60-9 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 1 h / 20 °C 1.2: 2 h 2.1: hydroxylamine hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 20 °C 3.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / water; tetrahydrofuran / 0.17 h / 20 °C 3.2: 20 °C 3.3: pH 6 - 7 4.1: hydrogenchloride; water / Reflux
	Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere 1.2: 2.25 h / 20 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 20 °C 3.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water / 0.17 h 3.2: 12 h 3.3: pH 6 - 7 4.1: hydrogenchloride; water / tetrahydrofuran / 12 h / Reflux 4.2: 20 °C / pH Ca_. 5

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2012/21476, 2012, A1
[2]Tanis, Steven P.; Colca, Jerry R.; Parker, Timothy T.; Artman, Gerald D.; Larsen, Scott D.; Gadwood, Robert C.; Zeller, James R. [Tetrahedron Letters, 2019, vol. 60, # 33]

5
[ 1359826-32-6 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 20 °C 2.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / water; tetrahydrofuran / 0.17 h / 20 °C 2.2: 20 °C 2.3: pH 6 - 7 3.1: hydrogenchloride; water / Reflux

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2012/21476, 2012, A1

6
[ 1359826-34-8 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 5-({4-[2-(hydroxyimino)-2-(3-methoxyphenyl)ethoxy]phenyl}methyl)-2,4-thiazolidinedione With hydrogenchloride; water In tetrahydrofuran for 12h; Reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃;	5-({4-[2-(3-Methoxyphenyl)-2-oxoethoxy]phenyl}methyl)-2,4-thiazolidinedione 3. A stirring solution of 24 (2.32g, 6.0 mmol) in THF (15mL) was treated with 6M aq. HCl (15mL) was warmed to reflux and maintained for 12 hours. The mixture was cooled to room temperature and 2N aq. NaOH was added until the pH was ca. 5.0. The mixture was extracted with EtOAc (2 x 75mL) and the combined organic layers were washed with brine (150 mL) and dried (Na2SO4). Concentrationin vacuo gave crude 3 as a light yellow semi-solid. Crude 3 was purified by chromatography was purified by chromatography on a column of silica gel using the flash technique (50 mm OD, 150g, 230-400 mesh), eluting with 0-15% EtOAc-CH2Cl2. Fractions containing 3 were pooled to give 3 (1.85g, 83%) as an ivory solid. Spectral and physicochemical data were identical to our prior report.3
	With hydrogenchloride; water Reflux;	4 A stirring solution of 5-(4- { [(2Z)-2-(hydroxyimino)-2-(3- methoxyphenyl)ethyl]oxy}benzyl)-l,3-thiazolidine-2,4-dione (0.76 g, 2.0 mmol; Supplier = Kalexsyn; Lot = 1003-TTP-124) in THF (5ml) and 6M HCI (5ml) was heated to reflux. Little reaction after 4 hours at reflux. Left to reflux overnight. Reaction is complete. 2N NaOH was added until the reaction mixture was ca. pH 8-9. The reaction mixture was extracted with EtOAc (2x25ml). The combined extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo to give a light yellow oily solid. This material was treated with 5% MeOH/ DCM (10ml) and the resulting white solids were collected by suction filtration and dried to afford 495mg of final product. Ή-NMR (DMSO-d6): δ 12.03(s, 1H), 7.62(d, J=7.7Hz, 1H), 7.49((m, 2H), 7.27(dd, J=8.2, 2.6Hz, 1H), 7.15(d, J=8.7Hz, 2H), 6.91(d, J=8.5Hz, 2H), 5.55(s, 2H), 4.88(dd, J= .1, 4.3Hz, 1H), 3.83(s, 3H), 3.31(m, 1H), 3.31(m, 1H0, 3.05(dd, J=14.1, 9.3Hz, 1H). HPLC: 3.782min., 93area% @ 210nm; 3.785min. 100area% @ 254nm. MS (ESI-) for Ci9Hi7N05S m/z 370.1 (M-H)

Reference： [1]Tanis, Steven P.; Colca, Jerry R.; Parker, Timothy T.; Artman, Gerald D.; Larsen, Scott D.; Gadwood, Robert C.; Zeller, James R. [Tetrahedron Letters, 2019, vol. 60, # 33]
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2012/21476, 2012, A1 Location in patent: Page/Page column 37-38

7
[ 32017-77-9 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium hydroxide / toluene; water / 78 °C 2: piperidine / ethanol / Reflux 3: cobalt(II) chloride hexahydrate; sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl / water; tetrahydrofuran 4: dimethyl sulfoxide; triethylamine; phosphorus pentoxide / dichloromethane / 2 h / 0 - 20 °C
	Multi-step reaction with 4 steps 1: sodium hydroxide / toluene / 78 °C 2: piperidine / ethanol / Reflux 3: sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl; cobalt(II) chloride / tetrahydrofuran; water 4: dimethyl sulfoxide; phosphorus pentoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2014/93114, 2014, A1
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2

8
[ 626-20-0 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: acetic acid; N-Bromosuccinimide / water; 1,4-dioxane / 0 - 20 °C 1.2: 20 °C 2.1: sodium hydroxide / toluene; water / 78 °C 3.1: piperidine / ethanol / Reflux 4.1: cobalt(II) chloride hexahydrate; sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl / water; tetrahydrofuran 5.1: dimethyl sulfoxide; triethylamine; phosphorus pentoxide / dichloromethane / 2 h / 0 - 20 °C
	Multi-step reaction with 5 steps 1: acetic acid; N-Bromosuccinimide / water; 1,4-dioxane / 0 - 20 °C 2: sodium hydroxide / toluene / 78 °C 3: piperidine / ethanol / Reflux 4: sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl; cobalt(II) chloride / tetrahydrofuran; water 5: dimethyl sulfoxide; phosphorus pentoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2014/93114, 2014, A1
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2

9
[ 1133820-08-2 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: piperidine / ethanol / Reflux 2: cobalt(II) chloride hexahydrate; sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl / water; tetrahydrofuran 3: dimethyl sulfoxide; triethylamine; phosphorus pentoxide / dichloromethane / 2 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: piperidine / ethanol / Reflux 2: sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl; cobalt(II) chloride / tetrahydrofuran; water 3: dimethyl sulfoxide; phosphorus pentoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2014/93114, 2014, A1
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2

10
[ 1133820-09-3 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: cobalt(II) chloride hexahydrate; sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl / water; tetrahydrofuran 2: dimethyl sulfoxide; triethylamine; phosphorus pentoxide / dichloromethane / 2 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate; acetic acid; [2,2]bipyridinyl; cobalt(II) chloride / tetrahydrofuran; water 2: dimethyl sulfoxide; phosphorus pentoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - WO2014/93114, 2014, A1
[2]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2

11
[ 1133819-87-0 ]
sodium 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-2,4-dioxo-1,3-thiazolidin-3-ide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium t-butanolate In tetrahydrofuran at 20℃; for 2h;	10B3 Example 10B3 Sodium 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-2,4-dioxo-1,3-thiazolidin-3-ide 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione (100 mg, 0.27 mmol) was suspended in THF (3 ml) and the mixture was heated with a heat gun until all solids dissolved. Added sodium tert-butoxide (26 mg, 0.27 mmol). Stirred at RT for 2 hours. Evaporated in vacuo. Dried under high vac. (ca. 50° C.) for 2 hours to give an off-white solid (110 mg, 100%). Analytical Calc. for C19H16NNaO5S plus 1.60% H2O: C, 57.08; H, 4.21; N, 3.50. Found: C, 56.91; H, 4.01; N, 3.30.

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2 Location in patent: Page/Page column 137

12
[ 1133819-87-0 ]
potassium 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-2,4-dioxo-1,3-thiazolidin-3-ide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2h;	10B4 Example 10B4 Potassium 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-2,4-dioxo-1,3-thiazolidin-3-ide A stirring suspension of 5-{4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione in THF (3 ml) was heated with a heat gun until all solids dissolved. Added a 1M solution of potassium tert-butoxide in THF (0.27 ml, 0.27 mmol). Stirred for 2 hours at RT. Evaporated in vacuo. Dried under high vac (ca. 50° C.) for 2 hours to give a salmon-colored solid (110 mg, 100%). Analytical Calc. for C19H16K1N1O5S plus 2.50% H2O and 7.96% KOH: C, 49.84; H, 3.96; N, 3.06. Found: C, 49.65; H, 3.58; N, 3.07.

Reference： [1]Current Patent Assignee: CIRIUS THERAPEUTICS - US9126959, 2015, B2 Location in patent: Page/Page column 137; 138

13
[ 123-08-0 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 12 h / 20 °C / Inert atmosphere 2: piperidine / ethanol / 12 h / Reflux; Inert atmosphere 3: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux
	Multi-step reaction with 5 steps 1.1: piperidine; benzoic acid / toluene / 1.5 h / Dean-Stark; Inert atmosphere; Reflux 2.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere 2.2: 2.25 h / 20 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 20 °C 4.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water / 0.17 h 4.2: 12 h 4.3: pH 6 - 7 5.1: hydrogenchloride; water / tetrahydrofuran / 12 h / Reflux 5.2: 20 °C / pH Ca_. 5

14
[ 1133819-87-0 ]
[ 1245699-51-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With [RhCl₂(p-cymene)]2; acetic acid; triethylamine; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide In N,N-dimethyl-formamide; isopropyl alcohol for 24h; Inert atmosphere; Reflux; stereoselective reaction;	20 6.20. 5-[[4-[(2S)-2-Hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4thiazolidinedione 14 A stirring mixture of dichloro(η6-p-cymene)ruthenium(II) dimer(8.1 mg, 0.000090 mmol), (1S, 2S)-(+)N-p-tosyl-1,2,diphenylethylenediamine(9.6 mg, 0.000026 mmol), and triethyl amine (20 μL,0.0001 mmol) in isopropyl alcohol (5.0 mL) was heated to reflux undernitrogen for 30 min. The mixture was then allowed to cool to roomtemperature and was concentrated in vacuo to afford a dark brownsolid. The dark brown solid was dissolved in DMF (5 mL) and ketone 7(0.55 g, 1.5 mmol) was added in 1 portion followed by HCOOH/Et3N(5:2, 0.55 g). The mixture was allowed to stir under nitrogen for 24 h, atwhich time HPLC analysis indicated that the reaction was complete.The mixture was concentrated in vacuo (hi-vac rotary evaporator) andthe residue was partitioned between saturated aq. NaHCO3 (75 mL) andCH2Cl2 (75 mL). The aqueous phase was extracted with CH2Cl2 (75 mL)and the combined organic phases were washed with water(2×100 mL), brine (2×100 mL) and dried (Na2SO4). Concentrationin vacuo afforded the crude alcohol 11 as a reddish foamy solid whichwas purified by chromatography on a column of silica gel using theflash technique (20mm OD, 30 g, 230-400 mesh), eluting with 0-20%acetone/CH2Cl2. Fractions containing 13 were pooled and concentratedin vacuo to provide 0.53 g (96%) of 14 as an off-white solid. 1H NMR(400 MHz, CDCl3): δ=7.93 (brs, 1), 7.31 (t, J=10.8 Hz, 1), 7.16 (m,2), 7.02 (m, 2), 6.85-6.95 (3), 5.11 (dd, J=11.6, 4.0 Hz, 1), 4.51 (dd,J=12.4, 5.2 Hz, 1), 4.11 (dd, J=12.4, 5.2 Hz, 1), 4.01 (m, 1), 3.84 (s,3), 3.45 (dd, J=18.8, 4.0 Hz, 1), 3.13 (dd, J=18.8, 11.6 Hz, 1); MS(ESI+) m/z 396.1 (M+Na), MS (ESI-) m/z 372.1 (M-H);[α]D25=-34° (c 11.0 CHCl3); Anal. Calcd. for C19H19NO5S: C, 61.11;H, 5.13; N, 3.75. Found: C, 61.23; H, 5.29; N, 3.71; Chiral HPLC(Chirobiotic T): 2:98, 96%ee.

15
[ 1133819-87-0 ]
[ 1245699-53-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With [RhCl₂(p-cymene)]2; acetic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine In N,N-dimethyl-formamide; isopropyl alcohol for 24h; Reflux; Inert atmosphere; stereoselective reaction;	19 6.19 . 5-[[4-[(2S)-2-Hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4thiazolidinedione 13 A stirring mixture of dichloro(η6-p-cymene)ruthenium(II) dimer(7.5 mg, 0.0000125 mmol), (1R, 2R)-(-)N-p-tosyl-1,2,diphenylethylenediamine(8.9 mg, 0.000025 mmol), and triethyl amine (20 μL,0.0001 mmol) in isopropyl alcohol (5.0 mL) was heated to reflux undernitrogen for 30 min. The mixture was then allowed to cool to roomtemperature and was concentrated in vacuo to afford a dark brownsolid. The dark brown solid was dissolved in DMF (5 mL) and ketone 7(0.50 g, 1.00 mmol) was added in 1 portion followed by HCOOH/Et3N(5:2, 0.51 g). The mixture was allowed to stir under nitrogen for 24 h, atwhich time HPLC analysis indicated that the reaction was complete.The mixture was concentrated in vacuo (hi-vac rotary evaporator) andthe residue was partitioned between saturated aq. NaHCO3 (75 mL) andCH2Cl2 (75 mL). The aqueous phase was extracted with CH2Cl2 (75 mL)and the combined organic phases were washed with water(2×100 mL), brine (2×100 mL) and dried (Na2SO4). Concentrationin vacuo afforded the crude alcohol 11 as a reddish foamy solid whichwas purified by chromatography on a column of silica gel using theflash technique (20mm OD, 30 g, 230-400 mesh), eluting with 0-20%acetone/CH2Cl2. Fractions containing 13 were pooled and concentratedin vacuo to provide 0.50 g (98%) of 13 as an off-white solid. 1H NMR(400 MHz, CDCl3): δ=7.93 (brs, 1), 7.31 (t, J=10.8 Hz, 1), 7.16 (m,2), 7.02 (m, 2), 6.85-6.95 (3), 5.11 (dd, J=11.6, 4.0 Hz, 1), 4.51 (dd,J=12.4, 5.2 Hz, 1), 4.11 (dd, J=12.4, 5.2 Hz, 1), 4.01 (m, 1), 3.84 (s,3), 3.45 (dd, J=18.8, 4.0 Hz, 1), 3.13 (dd, J=18.8, 11.6 Hz, 1); MS(ESI+) m/z 396.1 (M+Na), MS (ESI-) m/z 372.1 (M-H); [α]D25=38° (c 11.0 CHCl3); Anal. Calcd. for C19H19NO5S: C, 61.11; H,5.13; N, 3.75. Found: C, 61.14; H, 5.25; N, 3.66; Chiral HPLC(Chirobiotic T): 98.2, 96%ee.

16
[ 901414-51-5 ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: piperidine / ethanol / 12 h / Reflux; Inert atmosphere 2: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux

17
5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methylene]-2,4-thiazolidinedione [ No CAS ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux
	Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 20 °C 2.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water / 0.17 h 2.2: 12 h 2.3: pH 6 - 7 3.1: hydrogenchloride; water / tetrahydrofuran / 12 h / Reflux 3.2: 20 °C / pH Ca_. 5

18
5-({4-[2-(hydroxyimino)-2-(3-methoxyphenyl)ethoxy]phenyl}methylene)-2,4-thiazolidinedione [ No CAS ]
[ 1133819-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water / 0.17 h 1.2: 12 h 1.3: pH 6 - 7 2.1: hydrogenchloride; water / tetrahydrofuran / 12 h / Reflux 2.2: 20 °C / pH Ca_. 5

Reference： [1]Tanis, Steven P.; Colca, Jerry R.; Parker, Timothy T.; Artman, Gerald D.; Larsen, Scott D.; Gadwood, Robert C.; Zeller, James R. [Tetrahedron Letters, 2019, vol. 60, # 33]

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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
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H223	Flammable aerosol
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H251	Self-heating; may catch fire
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H302	Harmful if swallowed
H303	May be harmful if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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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
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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
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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

[ CAS No. 1133819-87-0 ] {[proInfo.proName]}

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[ 1133819-87-0 ] Synthesis Path-Downstream 1~18

Similar Product of [ 1133819-87-0 ]

Related Functional Groups of [ 1133819-87-0 ]

Aryls

Ethers

Amides

Thioesters

Related Parent Nucleus of [ 1133819-87-0 ]

Thiazolidines

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Response

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