[ CAS No. 100063-22-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 100063-22-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100063-22-7 ]

SDS Specification

Alternatived Products of [ 100063-22-7 ]

Product Details of [ 100063-22-7 ]

CAS No. :	100063-22-7	MDL No. :	MFCD00068161
Formula :	C₁₂H₁₁NO₂S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QESSCNMSOLRYBO-UHFFFAOYSA-N
M.W :	233.29	Pubchem ID :	700562
Synonyms :

Safety of [ 100063-22-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 100063-22-7 ]

* 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 [ 100063-22-7 ]

[ 100063-22-7 ] Synthesis Path-Downstream 1~14

1
[ 1943-83-5 ]
[ 100063-22-7 ]
[ 126080-13-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 2091 - 2102

2
[ 100063-22-7 ]
[ 113387-58-9 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 1; Methyl 3-chlorosulfonyl-5-phenyl-2-thiophenecarboxylate; Methyl 3-amino-5-phenyl-2-thiophenecarboxylate (5 g, manufactured by AK Scientific, Inc.) was dissolved in 20% hydrochloric acid (12 ml), and sodium nitrite (1.5 g, manufactured by Wako Pure Chemical Industries, Ltd.) dissolved in water (3.2 ml) under ice cooling was dripped to the resultant solution, and the resultant reaction solution was stirred for 1 hour. An acetic acid solution in which sulfur dioxide (2.5 g) and copper chloride (530 mg, manufactured by KANTO CHEMICAL CO., INC.) were dissolved was slowly added to the solution, and the resultant reaction solution was stirred for 5 hours. The reaction mixture was poured into ice water (100 ml), and a product was extracted with dichloromethane (100 ml), dried with magnesium sulfate and then concentrated to give 6.5 g of the titled compound.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2111 - 2116
[2]European Journal of Medicinal Chemistry,1988,vol. 23,p. 329 - 334
[3]Patent: US2009/192154,2009,A1 .Location in patent: Page/Page column 102

3
[ 100063-22-7 ]
[ 26118-67-2 ]
[ 123420-33-7 ]

Reference： [1]Synthesis,1989,p. 280 - 282

4
[ 124-42-5 ]
[ 100063-22-7 ]
[ 156424-47-4 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4288 - 4312

5
[ 100063-22-7 ]
[ 4755-77-5 ]
3-(ethoxyoxalyl-amino)-5-phenyl-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4443 - 4459

6
[ 100063-22-7 ]
3-chloro-5-phenylthiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3914 - 3929

7
[ 75-30-9 ]
[ 100063-22-7 ]
[ 478028-16-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 797 - 800

8
[ 75-44-5 ]
[ 100063-22-7 ]
[ 478028-43-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide; In water; toluene;	Example 119A 6-phenyl-2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione Methyl-3-amino-5-phenylthiophene-2-carboxylate (0.25 g, 1.07 mmol) in water (6 mL) was reacted with potassium hydroxide (0.12 g, 2.14 mmol) at 90 C. for 24 hours. The reaction was cooled to 0 C. and phosgene (1.9M in toluene, 0.70 mL, 1.40 mmol) was added dropwise. After stirring at room temperature for 1 hour, the resulting solid was collected by filtration, washed with excess water and dried to give the title compound as a tan solid (0.175 g, 65%).
65%		methyl-3-amino-5-phenylthiophene-2-carboxylate (0.25 g, 1.07 mmol) in water (6 ML) was reacted with potassium hydroxide (0.12 g, 2.14 mmol) at 90 C. for 24 hours.The reaction was cooled to 0 C. and phosgene (1.9M in toluene, 0.70 ML, 1.40 mmol) was added dropwise.After stirring at room temperature for 1 hour, the resulting solid was collected by filtration, washed with excess water and dried to give the title compound as a tan solid (0.175 g, 65%).
65%		6-phenyl-2H-thieno [3,2-d][1,3]oxazine-2,4(1H)-dione methyl-3-amino-5-phenylthiophene-2-carboxylate (0.25 g, 1.07 mmol) in water (6 ML) was reacted with potassium hydroxide (0.12 g, 2.14 mmol) at 90 C. for 24 hours.The reaction was cooled to 0 C. and phosgene (1.9M in toluene, 0.70 ML, 1.40 mmol) was added dropwise.After stirring at room temperature for 1 hour, the resulting solid was collected by filtration, washed with excess water and dried to give the title compound as a tan solid (0.175 g, 65%).

Reference： [1]Tetrahedron,2003,vol. 59,p. 10051 - 10057
[2]Patent: US2004/162285,2004,A1
[3]Patent: US2004/87577,2004,A1 .Location in patent: Page 71
[4]Patent: US2004/167123,2004,A1 .Location in patent: Page/Page column 104

9
[ 88-49-3 ]
[ 100063-22-7 ]
3-(4-chloro-2,5-dimethyl-benzenesulfonylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 793 - 796
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5333 - 5337

10
[ 874-60-2 ]
[ 100063-22-7 ]
[ 477326-18-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 797 - 800

11
[ 100063-22-7 ]
[ 99972-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; water; for 3h;Reflux;	General procedure: The 5-aryl-3-amino-2-carboxylic acid methyl ester (16.6 mmol) was added to a solution of KOH (60 mL, 0.6 M inH2O) and MeOH (60 mL). The mixture was heated to reflux for 3 h,concentrated, and washed with EtOAc (2 50 mL). The aqueous layer was cooled with ice and acidified by addition of a saturated aqueous solution of KHSO4. The precipitated solid was collected by filtration, washed with H2O (2 30 mL) and dried under reduced pressure over CaCl2.
	With potassium hydroxide; In tetrahydrofuran; methanol; water; for 3h;Reflux;	General procedure: The 5-Aryl-3-amino-2-carboxylic acid methyl ester (16.6 mmol) was added to a solution of KOH (60 mL, 0.6 M in H2O) and MeOH (60 mL). The mixture was heated to reflux for 3 h, concentrated, and washed with EtOAc (2 x 50 mL). The aqueous layer was cooled with ice and acidified with a saturated aqueous solution of KHSO4.The precipitated solid was collected by filtration, washed with H2O (2 x 30 mL) and dried under reduced pressure over CaCl2.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 797 - 800
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2817 - 2822
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5333 - 5337
[4]European Journal of Medicinal Chemistry,2013,vol. 65,p. 223 - 231
[5]European Journal of Medicinal Chemistry,2015,vol. 96,p. 14 - 21

12
[ 100063-22-7 ]
[ 74-88-4 ]
[ 478028-07-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 797 - 800

13
[ 116-11-0 ]
[ 100063-22-7 ]
[ 478028-16-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; for 2h;	To a stirred solution of 3-Amino-5-phenyl-thiophene-2- carboxylic acid methyl ester (1.82 g, 7.8 mmol) in 1, 2- dichloroethane (40 mL) was added sequentially 2- methoxypropene (3.0 mL, 31.2 mmol), ACOH (1.8 mL, 31.2 mmol) and NaBH (OAc) 3 (3.31 g, 15.6 mmol) and stirred for 2 hrs. It was then diluted with EtOAc and H 20. The aqueous solution was adjusted to pH = 7 by adding NAHCO3. The aqueous phase was extracted with EtOAc, the combined extract was washed with brine and dried on MGS04 and filtered. Purification on bond elute with hexane to 5% EtOAc-hexane furnished 3-Isopropylamino-5- phenyl-thiophene-2-carboxylic acid methyl ester (2.07 g, 96% yield NMR (CDC1 3, 400 MHz): 8 7.62 (d, 2H), 7.40 (m, 3H) 6.91 (s, 1H), 3.84 (s, 3H), 3.71 (m, 1H), 1. 35 (d, 6H).
		To a solution of S-amino-δ-phenyl-thiophene^-carboxylic acid methyl ester (4.92 g, 21.1 mmol) in DCM (1 10 mL) was added 2-methoxypropene (8.23 mL, 84.4 mmol), acetic acid (4.83 mL, 84.4 mmol) and sodium triacetoxyborohydride (8.94 g, 42.2 mmol) and the mixture <n="38"/>stirred overnight. Ethyl acetate and water were added, the aqueous phase adjusted to pH7 using sodium bicarbonate and then extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulphate. The crude product was purified by silica chromatography using a Flashmaster Personal apparatus (Argonaut) eluting with DCM / cyclohexane (1 :4) to give the title compound. MS calcd for (C15H17NO2S+ H)+: 276 MS found (electrospray): (M+H)+ =276
		To a solution of S-amino-δ-phenyl-thiophene^-carboxylic acid methyl ester (4.92 g, 21.1 mmol) in DCM (1 10 ml.) was added 2-methoxypropene (8.23 ml_, 84.4 mmol), acetic acid (4.83 ml_, 84.4 mmol) and sodium triacetoxyborohydride (8.94 g, 42.2 mmol) and the mixture stirred overnight. Ethyl acetate and water were added, the aqueous phase adjusted to pH7 using sodium bicarbonate and then extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulphate. The crude product was purified by silica chromatography using a Flashmaster Personal apparatus (Argonaut) eluting with DCM / cyclohexane (1 :4) to give the title compound. MS calcd for (Ci5H17NO2S+ H)+: 276 MS found (electrospray): (M+H)+ =276

Intermediate 30 Methyl 3-[(1 -methylethyljaminol-δ-phenyl^-thiophenecarboxylateTo a solution of S-amino-δ-phenyl-thiophene^-carboxylic acid methyl ester (4.92 g, 21.1 mmol) in DCM (1 10 ml.) was added 2-methoxypropene (8.23 ml_, 84.4 mmol), acetic acid (4.83 ml_, 84.4 mmol) and sodium triacetoxyborohydride (8.94 g, 42.2 mmol) and the mixture stirred overnight. Ethyl acetate and water were added, the aqueous phase adjusted to pH7 using sodium bicarbonate and then extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulphate. The crude product was <n="46"/>purified by silica chromatography using a Flashmaster Personal apparatus (Argonaut) eluting with DCM / cyclohexane (1 :4) to give the title compound. MS calcd for (C15H17NO2S+ H)+: 276 MS found (electrospray): (M+H)+ =276

Reference： [1]Synlett,2005,p. 583 - 586
[2]Patent: WO2004/52885,2004,A1 .Location in patent: Page 75-76
[3]Patent: WO2007/71434,2007,A1 .Location in patent: Page/Page column 36-37
[4]Patent: WO2008/43791,2008,A2 .Location in patent: Page/Page column 42
[5]Patent: WO2009/818,2008,A1 .Location in patent: Page/Page column 44-45

14
[ 100063-22-7 ]
[ 1000409-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With phenyltrimethylammonium tribromide; calcium carbonate; In methanol; dichloromethane;	EXAMPLE 8A methyl 3-amino-4-bromo-5-phenylthiophene-2-carboxylate To a mixture of <strong>[100063-22-7]methyl 3-amino-5-phenylthiophene-2-carboxylate</strong> (2.33 g, 10 mmol) and phenyltrimethylammonium tribromide (9.4 g, 25 mmol) in dichloromethane (25 mL) and methanol (25 mL) was added calcium carbonate (4.03 g, 40 mmol) and the mixture stirred overnight. The solid was filtered off and the filtrate concentrated. The residue was purified by flash chromatography on silica gel using 1:10 ethyl acetate/hexanes to give 2.75 g of the title compound. 1H NMR (DMSO-d6) δ 7.62-7.65 (m, 2H), 7.47-7.51 (m, 3H), 3.80 (s, 3H).
	With phenyltrimethylammonium tribromide; calcium carbonate; In methanol; dichloromethane;	EXAMPLE 8A methyl 3-amino-4-bromo-5-phenylthiophene-2-carboxylate To a mixture of <strong>[100063-22-7]methyl 3-amino-5-phenylthiophene-2-carboxylate</strong> (2.33 g, 10 mmol) and phenyltrimethylammonium tribromide (9.4 g, 25 mmol) in dichloromethane (25 mL) and methanol (25 mL) was added calcium carbonate (4.03 g, 40 mmol) and the mixture stirred overnight. The solid was filtered off and the filtrate concentrated. The residue was purified by flash chromatography on silica gel using 1:10 ethyl acetate/hexanes to give 2.75 g of the title compound. 1H NMR (DMSO-d6) δ 7.62-7.65 (m, 2H), 7.47-7.51 (m, 3H), 3.80 (s, 3H).
	With bromine; acetic acid; at 60℃; for 0.75h;	Step 8A: To a solution of methyl-3-amino-5-phenyl thiophene-2-carboxylate (1.0 g, 4.10 mmol) in HOAc (15.0 mL) was added Br2 (0.63 mL, 12.3 mmol). The reaction was heated to 60 C. and allowed to stir approximately 45 minutes, after which it was judged complete by LCMS. The excess Br2 was quenched with excess Na2S2O3, and the crude product was extracted (3*25 mL) into DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo, affording 1.6 g of crude methyl 3-amino-4-bromo-5-phenylthiophene-2-carboxylate as a light yellow solid >90% purity. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 3.87 (s, 3 H) 5.74 (br. s, 2 H) 7.41-7.49 (m, 3 H) 7.63-7.68 (m, 2 H); LCMS: m/e=282.1 [M+H]+

Reference： [1]Patent: US2008/161559,2008,A1 .Location in patent: Page/Page column 10
[2]Patent: US2008/161578,2008,A1 .Location in patent: Page/Page column 10-11
[3]Patent: US2008/4325,2008,A1 .Location in patent: Page/Page column 23

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Technical Information

• Acyl Group Substitution • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction

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P222	Do not allow contact with air.
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P233	Keep container tightly closed.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P320
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P321
P322
P330	Rinse mouth.
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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. 100063-22-7 ] {[proInfo.proName]}

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[ 100063-22-7 ] Synthesis Path-Downstream 1~14

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