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Quality Control of [ 1174429-23-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1174429-23-2 ]

CAS No. :	1174429-23-2	MDL No. :	MFCD26744038
Formula :	C₁₁H₁₀BrNO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	316.18	Pubchem ID :	-
Synonyms :

Safety of [ 1174429-23-2 ]

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Application In Synthesis of [ 1174429-23-2 ]

* 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 [ 1174429-23-2 ]

[ 1174429-23-2 ] Synthesis Path-Downstream 1~20

1
[ 1174429-23-2 ]
2.3-dihydro-1,4-benzodioxin-6-ylboronic acid [ No CAS ]
[ 1174428-47-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

2
[ 945756-49-0 ]
[ 1174429-23-2 ]
[ 1174428-55-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,2-dimethoxyethane at 130℃; for 0.25h; Microwave irradiation;

Reference： [1]Morales, Guillermo A.; Garlich, Joseph R.; Su, Jingdong; Peng, Xiaodong; Newblom, Jessica; Weber, Kevin; Durden, Donald L. [Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1922 - 1939]

3
[ 302348-49-8 ]
[ 1174429-23-2 ]
[ 1174428-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,2-dimethoxyethane at 130℃; for 0.25h; Microwave irradiation;

4
[ 957060-89-8 ]
[ 1174429-23-2 ]
[ 1174428-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,2-dimethoxyethane at 130℃; for 0.25h; Microwave irradiation;

5
[ 1256355-29-9 ]
[ 1174429-23-2 ]
[ 1174428-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,2-dimethoxyethane at 130℃; for 0.25h; Microwave irradiation;

6
[ 182344-13-4 ]
[ 1174429-23-2 ]
[ 1174429-13-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

7
[ 1174429-23-2 ]
[ 279262-23-6 ]
[ 1174429-22-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

8
[ 1072945-86-8 ]
[ 1174429-23-2 ]
[ 1174429-24-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

9
[ 603122-41-4 ]
[ 1174429-23-2 ]
[ 1174429-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,2-dimethoxyethane at 130℃; for 0.25h; Microwave irradiation;

10
[ 1174429-23-2 ]
[ 182344-21-4 ]
[ 1174429-27-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

11
[ 95201-93-7 ]
[ 1174429-23-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939
[2]Patent: US9550790,2017,B2

12
[ 1174429-23-2 ]
[ 175883-60-0 ]
[ 1174429-31-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

13
[ 1174429-23-2 ]
[ 144432-85-9 ]
[ 1174429-34-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

14
[ 1174429-23-2 ]
[ 376584-63-3 ]
5-morpholino-3-(2H-pyrazol-3-yl)-4-oxa-1-thia-7-indenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 18h;	3-Bromo-5-morpholino-4-oxa-1thia-7indenone (Compound 126) (48 mg, 0.15 mmol), <strong>[376584-63-3]1H-pyrazole-5-boronic acid</strong> (21 mg, 0.18 mmol), Pd[PPh3]4 (20 mg., 0.015 mmol) were taken into a mixture of toluene (0.8 mL), H2O/EtOH 1:1 (0.9 mL) under stirring and heated to 80° C. for 18 hours. Then the reaction mixture was cooled and diluted with ethyl acetate (30 mL) and filtered. The filtrate was washed with water, dried (Na2SO4), filtered and concentrated to yield a eluting solid product (40 mg). The crude was perused by preparative TLC plate on silica gel, eluting with 30:70 v/v ethyl acetate: CH2Cl2 yielding (8 mg, 0.026 mmol. 18percent) of the final compound 129. HPLC (254 nm)-Rt 0.65 min. MS (ESI) mo/z 304.1 [M+H]+Purity=>95percent by UV (254 nm).

Reference： [1]Patent: US2015/344494,2015,A1 .Location in patent: Paragraph 0258

15
[ 1174429-23-2 ]
[ 1256359-09-7 ]
3-(1-methyl-1H-indazol-6-yl)-5-morpholino-4-oxa-1-thia-7-indenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90.0℃; for 2h;Inert atmosphere;	3-Bromo-5-morpholino-4-oxa-1thia-7indenone (Compound 126) (53 mg, 0.17 mmol), 4,4,5,5-tetramethyl-2-(1-methyl-1H-indazol-6yl)-1,3,2-dioxaborolane (87 mg, 0.34 mmol), were dissolved in toluene/EtOH (1.7 mL of a 2:1 v/v mixture) and treated with 2 M aqueous Na2CO3 (0.6 mL). The resulting mixture was degassed with nitrogen fiat 10 minutes. This was treated with Pd[Ph3P]4 (10 mg 8.4 mumol) and the resulting mixture was heated to 90 C. for 2 hours under a nitrogen atmosphere. The reaction mixture was cooled, diluted with ethyl acetate (20 mL) and filtered through a pad of Celite. The filtrate was washed with water (20 mL) and the organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to yield the crude material. This was purified by preparative TLC plate eluting with ethyl acetate. The plate was run three times. 3-(1-Methyl-1H-indazol-6-yl)-5-morpholino-4-oxa-1-thia-7-indenone (Compound 130) was obtained as a white solid (4 mg, 0.01 mmol, 6%). HPLC (254 nm)-Rt 3.09 min. MS (ESI) m/z 368.3 [M+H]+ Purity=94.6% by UV (254 nm).

Reference： [1]Patent: US2015/344494,2015,A1 .Location in patent: Paragraph 0259

16
[ 913835-70-8 ]
[ 1174429-23-2 ]
3-[p-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-5-morpholino-4-oxa-1-thia-7-indenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; acetonitrile at 80℃; for 3h; Inert atmosphere;	22 Synthesis of Compound 132 3-Bromo-5-morpholino-4-oxa-1thia-7indenone (compound 126) (100 mg, 0.3 mmol) and 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenylboronic acid (83 mg, 0.4 mmol) were dissolved inacetonitrile (2 mL) and treated with 2 M aqueous Na2CO3 (1 mL). The resulting mixture was degassed with nitrogen for 10 minutes. This was treated with Pd[Ph3P]4 (5.4 mg, 4.7 μmol) and the resulting mixture was heated to 80° C. for 3 hours under a nitrogen atmosphere. The reaction mixture was cooled, diluted with ethyl acetate (20 mL) and filtered through Celite. The filtrate was washed with water (20 mL) and the organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to yield the crude amine (65 mg). The crude compound was purified by preparative TLC using hexane/ethylacetate (50:50) The purification yielded 3-[p-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-5morpholino-4-oxa-1thia-7-indenone (compound 132) (5.2 mg, 0.01 mmol, 4%). HPLC (254 nm)-Rt 0.29 min. MS (ESI) m/z 396.2 [M+H]+. Purity>99.9% by UV (254 nm).

Reference： [1]Current Patent Assignee: SIGNALRX PHARMACEUTICALS INC. - US2015/344494, 2015, A1 Location in patent: Paragraph 0261

17
[ 363185-87-9 ]
[ 1174429-23-2 ]
methyl 2-amino-5-(5-morpholino-7-oxo-4-oxa-1-thia-3-indenyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 85℃; for 1h; Inert atmosphere;	12.3 Step 3: Methyl 2-amino-5-f5-morpholino-7-oxo-4-oxa-l-thia-3-indenyl)benzoate: 3-Bromo-5- mo holino-4-oxa-l-thia-7-indenone (158 mg, 0.5 mmol) and methyl 2-amino-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (208 mg, 0.75 mmol, 1.5 eq.) were dissolved in toluene :ethanol (2: 1 v/v, 5 mL). The mixture was treated with Na2C03 2M aqueous solution (1.7 mL) and deoxygenated by bubbling N2 for 10 minutes. Pd[PPh3]4 (29 mg, 0.025 mmol) was added and the mixture was heated to 85 °C for 1 hour in a closed vial. The cooled reaction mixture was diluted with EtOAc (50 mL) washed with water and brine. The aqueous layers were extracted once again with a CH2Cl2/iPrOH mixture (9: 1 v/v). The combined organics were dried over anhydrous MgS04, filtered and evaporated. The crude residue was triturated with Et20 and EtOAc and filtered to yield the pure title compound as a white solid. Yield = 140 mg (0.36 mmol, 73 %). LC/MS - HPLC (254 nm) - Rt 2.48 min. MS (ESI) m/z 387.2 [M + H]+. Purity = 98.0 % by UV (254 nm).

Reference： [1]Current Patent Assignee: SIGNALRX PHARMACEUTICALS INC. - WO2018/140730, 2018, A1 Location in patent: Paragraph 0225

18
[ 1174429-23-2 ]
[ 1352412-93-1 ]
[ 2241238-29-7 ]

Yield	Reaction Conditions	Operation in experiment
21%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water at 85℃; for 4h; Inert atmosphere;	14.3 Step 3: Methyl 5-amino-2-(5-morpholino-7-oxo-4-oxa-l-thia-3-indenyl)benzoate 3-Bromo-5- morpholino-4-oxa-l-thia-7-indenone (632 mg, 2.0 mmol) and methyl 5-amino-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (831 mg, 3.0 mmol, 1.5 eq.) were dissolved in dioxane or a mix of toluene :ethanol (2: 1 v/v, 20 mL). The mixture was treated with Na2C03 2M aqueous solution (6.7 mL) and deoxygenated by bubbling N2 for 10 minutes. Pd[PPh3]4 (116 mg, 0.1 mmol) was added and the mixture was heated to 85 °C for 4 hours. LCMS analysis indicated about 50% conversion to product. The cooled reaction mixture was diluted with EtOAc (100 mL), washed with water and then washed with brine. The aqueous layers were extracted once again with a CH2Cl2/iPrOH mixture (9: 1 v/v). The combined organics were dried over anhydrous MgS04, filtered and evaporated. The crude residue was triturated with Et20 and EtOAc and filtered to yield the pure title compound as a white solid. Yield = 162 mg (0.42 mmol, 21 %). LC/MS - HPLC (254 nm) - Rt 2.11 min. MS (ESI) m/z 387.3 [M + H]+. Purity = 98.0 % by UV (254 nm).

Reference： [1]Current Patent Assignee: SIGNALRX PHARMACEUTICALS INC. - WO2018/140730, 2018, A1 Location in patent: Paragraph 0227

19
[ 1174429-23-2 ]
[ 210907-84-9 ]
[ 1174428-30-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 85℃; for 2h; Inert atmosphere;	31.1 Step-1: 3-(3-Aminophenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one. A mixture of 3- bromo-5-mo holino-7H-thieno[3,2-b]pyran-7-one (0.404 g, 1.26 mmol) and 3-aminophenyl boronic ester (0.336 g, 1.51 mmol) was dissolved in toluene :ethanol (2: 1, v/v, 30 mL). The mixture was treated with aqueous 2.0 M Na2C03 (5.0 mL) and degassed under a flow of argon for 15 min. Pd(PPh3)4 (0.073 g, 0.063 mmol) was added, and the mixture again degassed for 10 min. The reaction mixture was next heated to 85 °C for 2.0 h in a closed vial. The reaction mixture was cooled to the ambient temperature, diluted with DCM (30 mL), washed with water (10 mL), and brine (10 mL). The water layer was extracted with DCM (2 x 10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica-gel), eluting with DCM/MeOH (95:5) gradient. The fractions containing the product were concentrated to yield 50% of 3-(3- aminophenyl)-5-mo holino-7H-thieno[3,2-b]pyran-7-one (0.206 g, 0.627 mmol). Physical state: Brown Solid. R/= 0.4 (mobile phase: 10% MeOH/DCM).

Reference： [1]Current Patent Assignee: SIGNALRX PHARMACEUTICALS INC. - WO2018/140730, 2018, A1 Location in patent: Paragraph 0244

20
[ 1155264-46-2 ]
[ 1174429-23-2 ]
5-morpholino-3-(1-oxa-4-aza-3,4-dihydro-2H-naphth-6-yl)-4-oxa-1-thia-7-indenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 90℃; for 4h;	1.2; 19.2 Step 2: 5-morpholino-3-(1-oxa-4-aza-3,4-dihydro-2H-naphth-6-yl)-4-oxa-1-thia-7-indenone A mixture of 3-bromo-5-morpholino-4-oxa-l-thia-7-indenone (1.68 g., 5.30 mmol) and 4, 4, 5, 5- tetramethyl-2-(l-oxa-4-aza-3,4-dihydro-2H-naphth-6-yl)-l,3,2-dioxaborolane (1.80 g, 6.89 mmol) Na2C03 2M aqueous solution (18 mL), toluene: ethanol 2: 1 v/v (55 mL) and Pd[Ph3P]4 (360 mg, 0.31 mmol) were stirred together at 90°C for 4 h. Then the reaction mixture was cooled and diluted with ethyl acetate (200 mL) and filtered. The filtrate was washed with water and dried (Na2S04), filtered and concentrated to yield crude which was purified on silica column using 0-5 % MeOH/EtOAc gradient system. Useful fractions were pulled together and concentrated to yield pure final product (950 mg, 48% yield).LC/MS - HPLC (254 nm) - Rt 2.34 min. MS (ESI) m/z 371.3 [M+ + H+] Purity = 98 % by UV (254 nm).

Reference： [1]Current Patent Assignee: SIGNALRX PHARMACEUTICALS INC. - WO2020/23340, 2020, A1 Location in patent: Paragraph 0179; 0197

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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

[ CAS No. 1174429-23-2 ] {[proInfo.proName]}

Quality Control of [ 1174429-23-2 ]

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Product Details of [ 1174429-23-2 ]

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Application In Synthesis of [ 1174429-23-2 ]

[ 1174429-23-2 ] Synthesis Path-Downstream 1~20

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