[ CAS No. 20699-85-8 ] {[proInfo.proName]}

Name: 20699-85-8|Methyl 5-aminobenzo[b]thiophene-2-carboxylate|98%
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Quality Control of [ 20699-85-8 ]

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SDS Specification

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Product Details of [ 20699-85-8 ]

CAS No. :	20699-85-8	MDL No. :	MFCD04123924
Formula :	C₁₀H₉NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SIMBULBEQVHFPK-UHFFFAOYSA-N
M.W :	207.25	Pubchem ID :	2824064
Synonyms :

Calculated chemistry of [ 20699-85-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.51
TPSA :	80.56 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	2.28
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	2.75
Consensus Log Po/w :	2.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.01
Solubility :	0.202 mg/ml ; 0.000972 mol/l
Class :	Soluble
Log S (Ali) :	-3.79
Solubility :	0.034 mg/ml ; 0.000164 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.07
Solubility :	0.178 mg/ml ; 0.000859 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.07

Safety of [ 20699-85-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20699-85-8 ]

* 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.

Upstream synthesis route of [ 20699-85-8 ]
Downstream synthetic route of [ 20699-85-8 ]

[ 20699-85-8 ] Synthesis Path-Upstream 1~4

1
[ 20699-86-9 ]
[ 20699-85-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; tin(ll) chloride In water at 80℃; for 1 h;	To the above product 6-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1 g, 0.004 mol) and SnCI₂-H₂O (4.85 g, 0.017 mol) was added concentrated HCI (20 ml_, 0.24 mol). The reaction was stirred at 80 ⁰C for 1 hour, then cooled to low temperature. Then, the pH of the reaction mixture was raised to pH = 9 ~ 11 using 10percent NaOH solution in water. The suspension was then filtered and residue was washed with H₂O followed by CH₃OH to yield the product as yellow solid quantitatively.
83%	With hydrogen In methanol for 2 h;	Synthesis of Benzofuran and Benzo [b] thiophene Derivatives; Synthesis of 5- (3-chloro-2-methvl-benzenesulfonylamino) -benzorblthiophene-2-carboxylic acid methyl ester, STX 971 (KRB01096) :; 5-amino-benzo [b] thiophene-2-carboxylic acid methyl ester (KRB01094) :; To a solution of 5-nitro-benzo [b] thiophene-2-carboxylic acid methyl ester [15] (130 mg, 0.548 mmol) in methanol (30 mL) was added 5percent palladium on carbon (20 mg) and the mixture was stirred under 1 atm Ha for 2 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica column to afford 5-amino- benzo [b] thiophene-2-carboxylic acid methyl ester as a pale yellow solid (94 mg, 83percent), single spot at Rf 0.75 (95: 5 dichloromethane : methanol).'H NMR (CDCl3) : No. 7.86 (1H, s), 7.61 (1H, d, J=8. 7 Hz), 7.11 (1H, d, J=2. 2 Hz), 6.88 (1H, dd, J=8.7, 2. 5 Hz), 3.91 (3H, s), 3.76 (2H, s, N-H2) [16].

Reference： [1] Patent: WO2006/101454, 2006, A1, . Location in patent: Page/Page column 45
[2] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 5, p. 1611 - 1618
[3] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6382 - 6394
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 9, p. 963 - 967
[5] Patent: WO2005/42513, 2005, A1, . Location in patent: Page/Page column 57-58
[6] Patent: US2004/142953, 2004, A1,
[7] Patent: US2005/288282, 2005, A1,
[8] Patent: US6897220, 2005, B2,
[9] Patent: EP2926660, 2015, A1, . Location in patent: Paragraph 0384

2
[ 6361-21-3 ]
[ 20699-85-8 ]

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6382 - 6394
[2] Patent: WO2006/101454, 2006, A1,

3
[ 20699-86-9 ]
[ 20699-85-8 ]

Reference： [1] Patent: US5863936, 1999, A,

4
[ 27996-87-8 ]
[ 20699-85-8 ]

Reference： [1] Patent: EP2926660, 2015, A1,

[ 20699-85-8 ] Synthesis Path-Downstream 1~88

1
[ 20699-85-8 ]
BOCNH-X-CONH-X-OR; mixture of [ No CAS ]
5-BOCNH-X-CONH-X-CONH-benzo[b]thiophen-2-yl-COOR; mixture of [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2049 - 2057

2
[ 20699-86-9 ]
[ 20699-85-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; tin(ll) chloride; In water; at 80℃; for 1h;	To the above product 6-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1 g, 0.004 mol) and SnCI2-H2O (4.85 g, 0.017 mol) was added concentrated HCI (20 ml_, 0.24 mol). The reaction was stirred at 80 0C for 1 hour, then cooled to low temperature. Then, the pH of the reaction mixture was raised to pH = 9 ~ 11 using 10% NaOH solution in water. The suspension was then filtered and residue was washed with H2O followed by CH3OH to yield the product as yellow solid quantitatively.
83%	With hydrogen;5%-palladium/activated carbon; In methanol; under 760.051 Torr; for 2h;	Synthesis of Benzofuran and Benzo [b] thiophene Derivatives; Synthesis of 5- (3-chloro-2-methvl-benzenesulfonylamino) -benzorblthiophene-2-carboxylic acid methyl ester, STX 971 (KRB01096) :; 5-amino-benzo [b] thiophene-2-carboxylic acid methyl ester (KRB01094) :; To a solution of 5-nitro-benzo [b] thiophene-2-carboxylic acid methyl ester [15] (130 mg, 0.548 mmol) in methanol (30 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm Ha for 2 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica column to afford 5-amino- benzo [b] thiophene-2-carboxylic acid methyl ester as a pale yellow solid (94 mg, 83%), single spot at Rf 0.75 (95: 5 dichloromethane : methanol).'H NMR (CDCl3) : No. 7.86 (1H, s), 7.61 (1H, d, J=8. 7 Hz), 7.11 (1H, d, J=2. 2 Hz), 6.88 (1H, dd, J=8.7, 2. 5 Hz), 3.91 (3H, s), 3.76 (2H, s, N-H2) [16].
	With hydrogenchloride; In methanol; ethyl acetate;	Step 2: Methyl-5-amino-benzo[b]thiophene-2-carboxylate (588) A suspension of 584 (3.52 g, 14.8 mmol) in methanol (100 ml) was treated with Fe powder (6.63 g, 118.7 mmol). The resulting suspension was heated to reflux, and 12M HCl (8.5 ml) was slowly added over 15 min. The resulting green dark suspension was refluxed for an additional 3 h, then cooled and concentrated. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, then brine, dried over MgSO4, filtered and concentrated to afford (2.57 g, 84%). 1H NMR: (DMSO) delta (ppm): 7.92 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.05 (d, J=1.5 Hz, 1H), 6.88 (dd, J=1.8, 8.4 Hz, 1H), 5.27 (s, 2H), 3.85 (s, 3H). LRMS: 207.0 (Calc.); 208.1 (found).

	With hydrogenchloride; In methanol; ethyl acetate;	Step 2: Methyl-5-amino-benzo[b]thiophene-2-carboxylate (588) A suspension of 584 (3.52 g, 14.8 mmol) in methanol (100 ml) was treated with Fe powder (6.63 g, 118.7 mmol). The resulting suspension was heated to reflux, and 12M HCl (8.5 ml) was slowly added over 15 min. The resulting green dark suspension was refluxed for an additional 3 h, then cooled and concentrated. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, then brine, dried over MgSO4, filtered and concentrated to afford (2.57 g, 84%). 1H NMR: (DMSO) delta (ppm): 7.92 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.05 (d, J=1.5 H, 1H), 6.88 (dd, J=1.8, 8.4 Hz, 1H), 5.27 (s, 2H), 3.85 (s, 3H). LRMS: 207.0 (Calc.); 208.1 (found).
	With hydrogenchloride; In methanol; ethyl acetate;	Step 2: Methyl-5-amino-benzo[b]thiophene-2-carboxylate (588) A suspension of 584 (3.52 g, 14.8 mmol) in methanol (100 ml) was treated with Fe powder (6.63 g, 118.7 mmol). The resulting suspension was heated to reflux, and 12M HCl (8.5 ml) was slowly added over 15 min. The resulting green dark suspension was refluxed for an additional 3 h, then cooled and concentrated. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, then brine, dried over MgSO4, filtered and concentrated to afford (2.57 g, 84%). 1H NMR: (DMSO) delta (ppm): 7.92 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.05 (d, J=1.5 Hz, 1H), 6.88 (dd, J=1.8, 8.4 Hz, 1H), 5.27 (s, 2H), 3.85 (s, 3H). LRMS: 207.0 (Calc.). 208.1 (found).

Reference： [1]Patent: WO2006/101454,2006,A1 .Location in patent: Page/Page column 45
[2]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1611 - 1618
[3]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[4]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 963 - 967
[5]Patent: WO2005/42513,2005,A1 .Location in patent: Page/Page column 57-58
[6]Patent: US2004/142953,2004,A1
[7]Patent: US2005/288282,2005,A1
[8]Patent: US6897220,2005,B2
[9]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0384

3
[ 20699-85-8 ]
[ 15944-88-4 ]
[ 449147-22-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1611 - 1618

4
[ 20699-85-8 ]
[ 24424-99-5 ]
[ 292068-72-5 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

5
[ 20699-85-8 ]
[ 66493-39-8 ]
5-(4-tert-butoxycarbonylamino-benzoylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

6
[ 20699-85-8 ]
[ 128293-64-1 ]
5-[(4-tert-butoxycarbonylamino-1-methyl-1H-imidazole-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 3h;	To a mixture of compound 133 (508 mg, 2.106 mmol) and compound 61 (300 mg, 1.404 mmol) in DMF (7.021 mL) was added EDC (567 mg, 2.81 mmol) and DMAP (429 mg, 3.51 mmol) at rt. After stirring for 3 h, the reaction was diluted with EtOAc and then washed with water, sat?d aq. NaHC03 and brine. The organic layer was dried over MgS04, filtered and concentrated to obtain compound 138, which was used in the next step without purification (0.6 g, 100% yield). LCMS = 8.36 min (15 min method). Mass observed (EST): 429.0 (M-H).
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a mixture of compound 4 (100 mg, 0.237 mmol) and compound 78 (132 mg, 0.355 mmol) indichloromethane (2.3 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (71.6 mg,0.355 mmol) and 4-dimethylaminopyridine (14.45 mg, 0.118 mmol) at room temperature. Afterstirring for 2 h, the mixture was extracted with dichloromethane and water. The organic layer wasdried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silicagel chromatography (dichloromethane/methanol), followed by RP-HPLC (C18 Kromasil,acetonitrile/water) to yield compound 18 (50 mg, 33% yield).

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Patent: WO2019/133652,2019,A1 .Location in patent: Page/Page column 138; 172
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2455 - 2458

7
[ 20699-85-8 ]
[ 107474-67-9 ]
7-(2-methoxycarbonyl-benzo[b]thiophen-5-ylcarbamoyl)-1,6-dihydro-2H-3,6-diaza-as-indacene-3-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

8
[ 20699-85-8 ]
[ 77716-11-1 ]
methyl-5-(4-((tert-butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxamido)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		A solution of 4-((tert-butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxylic acid (127 mg, 0.530 mmol) in N,N-dimethylformamide (i mL) was charged with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (185 mg, 0.960 mmol) and4-(dimethylamino)pyridine (147 mg, 1.20 mmol). The reaction mixture was stirred at room temperature for 4 h. Methyl 5-aminobenzo[b]thiophene-2-carboxylate (100 mg, 0.480 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. This was then poured onto ice-water (40 mL) and extracted withethyl acetate ( x 100 mL). The combined organic extracts were sequentially washed with an aqueous solution of citric acid (i M, 60 mL), a saturated aqueous solution of sodium hydrogen carbonate (70 mL), water (70 mL) and brine (70 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated to give the title compound (i8 mg, 90%) as a cream solid. The product was carried through to the nextstep without any further purification.MS (ES+): m/z = 430 (M+H) LCMS (Method B): tR = 4.07 mm.
75%		A solution of 4-((ieri-butoxycarbonyl)amino)-i-methyl-iH-pyrrole-2-carboxylic acid (500 mg, 2.1 mmol) in A V-dimethylformamide (10 mL) was charged with i-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (725 mg, 3.8 mmol) and 4- (dimethylamino)pyridine (577 mg, 4.7 mmol). The reaction mixture was stirred at room temperature for 2 h. Methyl 5-aminobenzo[]thiophene-2-carboxylate 17 (392 mg, 1.9 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. This was then poured into ice-water (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were sequentially washed with 1 M citric acid (30 mL), a saturated aqueous solution of sodium hydrogen carbonate (35 mL), water (35 mL) and brine (35 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography (silica), eluting with ethyl acetate/hexane (from 0% to 50%), to give the title compound 18 (610 mg, 75%) as a beige solid. (0901) MS (ES+): m/z = 430 (M+H)+; LCMS: tR = 7.90 min.
72%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃;	Compound 3 (255 mg, 1.062 mmol) and compound 4 (200 mg, 0.965 mmol) were dissolved in DMF (3.22 mL). EDC (222 mg, 1.158 mmol) was added to the reaction mixture, followed by DMAP (118 mg, 0.965 mmol) and the reaction was stirred at rt overnight. The reaction mixture was diluted with EtOAc and was washed with sat'd NH4Cl, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by silica gel chromatography (0% to 40% EtOAc/hexanes) to obtain compound 5 as an orange-white solid (300 mg, 0.699 mmol, 72% yield). LCMS = 6.014 min (8 min method). Mass observed (ESI+): 430.05 (M+H). 1H NMR (400 MHz, DMSO-i): d 1.46 (s, 9H), 3.83 (s, 3H), 3.89 (s, 3H), 6.97 (d, J = 8.8 Hz, 2H), 7.79 (d, J = 9.0 Hz, 1H), 7.97 (d, J = 8.9 Hz, 1H), 8.18 (s, 1H), 8.49 (s, 1H), 9.14 (s, 1H), 9.98 (s, 1H).

72%

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;

Compound 6 (255 mg, 1.062 mmol) and compound 7 (200 mg, 0.965 mmol) were dissolved indimethylformamide (3.22 mL). 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (222 mg, 1.158mmol) was added to the reaction mixture, followed by 4-dimethylaminopyridine (118 mg, 0.965mmol) and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and was washed with saturated ammonium chloride, brine, dried oversodium sulfate, filtered and concentrated. The crude product was purified by silica gelchromatography (0% to 40% ethyl acetate/hexanes) to obtain compound 7 as an orange-white solid(300 mg, 0.699 mmol, 72% yield).

Reference： [1]Patent: WO2017/32983,2017,A1 .Location in patent: Page/Page column 58; 59; 82; 83
[2]Patent: WO2016/198869,2016,A1 .Location in patent: Page/Page column 17
[3]Patent: WO2020/49286,2020,A1 .Location in patent: Page/Page column 184
[4]Patent: WO2019/133652,2019,A1 .Location in patent: Page/Page column 138; 139; 140; 141
[5]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2455 - 2458
[6]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

9
[ 20699-85-8 ]
[ 111331-82-9 ]
5-(3-tert-butoxycarbonylamino-benzoylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃;Inert atmosphere;	Compound 168 (1.259 g, 5.31 mmol) and compound 61 (1.00 g, 4.83 mmol) were dissolved in DMF (6.0 mL). EDC?HC1 (1.11 g, 0.476 mmol) and DMAP (0.295 g, 2.41 mmol) were added. The reaction mixture was allowed to stir at ft under Ar overnight. After stirring overnight, DI water (25 mL) was added to the reaction mixture to precipitate the product. The slurry was stirred at ft for 5 mm and was then filtered. The resulting solids were placed on high vacuum to dryness to give crude 169, which was used directly in the next step (2.058 g, 5.31 mmol, 100% yield). UPLCMS (2.5 mm method) = 1.84 mm. Mass observed (ESI): 427.2 (M+H).

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Patent: WO2019/133652,2019,A1 .Location in patent: Page/Page column 138; 139; 182

10
[ 20699-85-8 ]
[ 83673-98-7 ]
5-[(2-tert-butoxycarbonylamino-thiazole-4-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

11
[ 20699-85-8 ]
[ 292068-69-0 ]
5-[(4-tert-butoxycarbonylamino-thiophene-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

12
[ 20699-85-8 ]
[ 292069-98-8 ]
5-[(5-tert-butoxycarbonylamino-benzofuran-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

13
[ 20699-85-8 ]
[ 292068-77-0 ]
5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

14
[ 20699-85-8 ]
[ 138730-81-1 ]
5-[(5-tert-butoxycarbonylamino-1H-indole-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

15
[ 20699-85-8 ]
5-{4-[bis-(2-chloro-ethyl)-amino]-benzoylamino}-benzo[b]thiophene-2-carbonyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1611 - 1618

16
[ 20699-85-8 ]
[ 449147-16-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1611 - 1618

17
[ 20699-85-8 ]
3-[1-methyl-4[1-methyl-4[5-[4-N,N-bis(2-chloroethyl)aminobenzene-1-carboxamido]benzothiophene-2-carboxamido]-pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine hydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1611 - 1618

18
[ 20699-85-8 ]
3-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

19
[ 20699-85-8 ]
4-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

20
[ 20699-85-8 ]
4-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

21
[ 20699-85-8 ]
4-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

22
[ 20699-85-8 ]
2-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

23
[ 20699-85-8 ]
5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzofuran-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

24
[ 20699-85-8 ]
6-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzooxazole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

25
[ 20699-85-8 ]
5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

26
[ 20699-85-8 ]
5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-1H-benzoimidazole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

27
[ 20699-85-8 ]
5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

28
[ 20699-85-8 ]
6-(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

29
[ 20699-85-8 ]
5-amino-1H-indole-2-carboxylic acid [2-(1-methyl-5-methylcarbamoyl-1H-pyrrol-3-ylcarbamoyl)-benzo[b]thiophen-5-yl]-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

30
[ 20699-85-8 ]
5-amino-1H-indole-2-carboxylic acid [2-(5-dimethylcarbamoyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-benzo[b]thiophen-5-yl]-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

31
[ 20699-85-8 ]
5-amino-1H-indole-2-carboxylic acid {2-[5-(2-cyano-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-benzo[b]thiophen-5-yl}-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

32
[ 20699-85-8 ]
[ 292073-32-6 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

33
[ 20699-85-8 ]
[ 292073-33-7 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

34
[ 20699-85-8 ]
[ 292073-30-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

35
[ 20699-85-8 ]
5-amino-1H-indole-2-carboxylic acid {2-[5-(2-carbamimidoyl-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-benzo[b]thiophen-5-yl}-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

36
[ 20699-85-8 ]
4-[(5-[5-(4-dimethylamino-butyrylamino)-1H-indole-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

37
[ 20699-85-8 ]
[ 292073-34-8 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

38
[ 20699-85-8 ]
[ 292068-77-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

39
[ 20699-85-8 ]
4-({5-[(5-tert-butoxycarbonylamino-benzo[b]thiophene-2-carbonyl)-amino]-benzofuran-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

40
[ 20699-85-8 ]
6-(4-[5-(4-dimethylamino-butyrylamino)-benzo[b]thiophene-2-carbonyl]-amino}-thiophene-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

41
[ 20699-85-8 ]
4-[(5-amino-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

42
[ 20699-85-8 ]
[ 292070-89-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

43
[ 20699-85-8 ]
4-({5-[(4-amino-thiophene-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

44
[ 20699-85-8 ]
4-[5-(4-amino-benzoylamino)-benzo[b]thiophene-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

45
[ 20699-85-8 ]
4-({4-[(5-amino-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

46
[ 20699-85-8 ]
4-({5-[(2-amino-thiazole-4-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

47
[ 20699-85-8 ]
4-({5-[(4-amino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

48
[ 20699-85-8 ]
4-({5-[(4-amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

49
[ 20699-85-8 ]
4-[5-(3-amino-benzoylamino)-benzo[b]thiophene-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

50
[ 20699-85-8 ]
4-({5-[(5-amino-benzofuran-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

51
[ 20699-85-8 ]
4-({5-[(5-amino-1H-indole-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

52
[ 20699-85-8 ]
4-({5-[(5-amino-benzo[b]thiophene-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

53
[ 20699-85-8 ]
[ 292069-59-1 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

54
[ 20699-85-8 ]
[ 292069-61-5 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

55
[ 20699-85-8 ]
[ 292069-60-4 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

56
[ 20699-85-8 ]
[ 292069-58-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

57
[ 20699-85-8 ]
[ 292069-57-9 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

58
[ 20699-85-8 ]
[ 292069-62-6 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

59
[ 20699-85-8 ]
[ 292068-93-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

60
[ 20699-85-8 ]
6-{4-[(5-amino-benzo[b]thiophene-2-carbonyl)-amino]-thiophene-2-carbonyl}-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

61
[ 20699-85-8 ]
4-[(5-[2-(4-dimethylamino-butyrylamino)-thiazole-4-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

62
[ 20699-85-8 ]
4-({5-[3-(4-dimethylamino-butyrylamino)-benzoylamino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

63
[ 20699-85-8 ]
4-({5-[4-(4-dimethylamino-butyrylamino)-benzoylamino]-benzo[b]thiophene-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

64
[ 20699-85-8 ]
4-[(5-[4-(4-dimethylamino-butyrylamino)-thiophene-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

65
[ 20699-85-8 ]
4-[(5-[4-(4-dimethylamino-butyrylamino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

66
[ 20699-85-8 ]
4-[(5-[4-(4-dimethylamino-butyrylamino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

67
[ 20699-85-8 ]
[ 292069-65-9 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

68
[ 20699-85-8 ]
1-methyl-4-({5-[(3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carbonyl)-amino]-benzo[b]thiophene-2-carbonyl}-amino)-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

69
[ 20699-85-8 ]
4-[(4-[5-(4-dimethylamino-butyrylamino)-benzo[b]thiophene-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

70
[ 20699-85-8 ]
[ 292069-64-8 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

71
[ 20699-85-8 ]
4-[6-(5-amino-benzo[b]thiophene-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carbonyl]-amino}-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

72
[ 20699-85-8 ]
[ 292069-66-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

73
[ 20699-85-8 ]
4-[(5-[5-(4-dimethylamino-butyrylamino)-benzofuran-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

74
[ 20699-85-8 ]
4-[(5-[5-(4-dimethylamino-butyrylamino)-benzo[b]thiophene-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

75
[ 20699-85-8 ]
[ 292069-34-2 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

76
[ 20699-85-8 ]
[ 292069-88-6 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

77
[ 20699-85-8 ]
[ 292069-63-7 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

78
[ 20699-85-8 ]
5-(4-dimethylamino-butyrylamino)-1H-indole-2-carboxylic acid [2-(1-methyl-5-methylcarbamoyl-1H-pyrrol-3-ylcarbamoyl)-benzo[b]thiophen-5-yl]-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

79
[ 20699-85-8 ]
5-(4-dimethylamino-butyrylamino)-1H-indole-2-carboxylic acid [2-(5-dimethylcarbamoyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-benzo[b]thiophen-5-yl]-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

80
[ 20699-85-8 ]
(2-{2-[5-(4-dimethylamino-butyryl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-benzo[b]thiophen-5-ylcarbamoyl}-1H-indol-5-yl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

81
[ 20699-85-8 ]
[ 292069-54-6 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

82
[ 20699-85-8 ]
4-[(5-[6-(4-dimethylamino-butyryl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carbonyl]-amino}-benzo[b]thiophene-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

83
[ 20699-85-8 ]
4-({6-[5-(4-dimethylamino-butyrylamino)-benzo[b]thiophene-2-carbonyl]-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carbonyl}-amino)-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

84
[ 20699-85-8 ]
5-(4-dimethylamino-butyrylamino)-1H-indole-2-carboxylic acid {2-[5-(3-dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-benzo[b]thiophen-5-yl}-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394

85
[ 6361-21-3 ]
[ 20699-85-8 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6382 - 6394
[2]Patent: WO2006/101454,2006,A1

86
tin(II)chloride dihydrate [ No CAS ]
[ 20699-86-9 ]
[ 20699-85-8 ]

Yield	Reaction Conditions	Operation in experiment
8.564 g (96%)	In ethanol;	Preparation of Methyl 5-aminobenzo[b]thiophene-2-Carboxylate In a 250 ml round-bottomed flask fitted with a Teflon stirrer and a reflux condenser, methyl 5-nitrobenzo[b]thiophene-2-carboxylate (10 g, 42.18 mmole) was dissolved in ethanol (100 ml). Tin (II) chloride dihydrate (5 equivalents, 47.60 g, 211 mmole) was added in one lot and the resulting slurry was reluxed for 18 hours while being stirred. The reaction mixture was cooled to room temperature, transferred to a 2000 ml Erlenmeyer flask, and carefully quenched with 5% sodium bicarbonate solution (aprroximately 700 ml) until effervescense was no longer detected. The resulting precipitate was filtered off and air-dried. The dried solid was dissolved in hot ethanol (500 ml), and filtered to remove undissolved material. The filtrate was evaporated in vacuo to give 8.564 g (96%) of methyl 5-aminobenzo[b]thiophene-2-carboxylate.

Reference： [1]Patent: US5863936,1999,A

87
[ 20699-85-8 ]
[ 60656-87-3 ]
[ 910791-70-7 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a solution of compound IV (194 mg, 0.9 mmol) in 10 ml_ of MeOH was addedBenzyloxy acetaldehyde (0.086 ml_, 0.6 mmol) at room temperature. The resulting mixture was stirred overnight. NaCNBH3 (98 mg, 1.562 mmol) and acetic acid (1 ml_) were then added and the resulting mixture was stirred at room temperature for 2 hours. After work-up, the residue was purified on column (Hexanes: EtOAc = 4:1) to afford compound 5-(2-Benzyloxy-ethylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester, 20a-1. Yield: 84%. LCMS m/z: 342 ([M+H]+).

Reference： [1]Patent: WO2006/101454,2006,A1 .Location in patent: Page/Page column 56

88
[ 20699-85-8 ]
[ 103-80-0 ]
[ 910791-67-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a solution of above Benzothiophene amine (104 mg, 0.5 mmol) in 5 mL of anhydrous DCM was added phenylacetic acid chloride (0.13 mL, 1.0 mmol) and DIEA (di-isopropyl ethylamine, 0.18 mL, 2.0 mmol) at room temperature under N2. The resulting mixture was stirred overnight. After work-up, the residue was purified on column (Hexanes:DCM : EtOAc = 3:1 :1 ) to afford compound 5-Phenylacetylamino- benzo[b]thiophene-2-carboxylic acid methyl ester. Yield: 71 %. LCMS m/z: 326 ([M+H]+).
	With 4-methyl-morpholine; In tetrahydrofuran; dichloromethane; at 20℃; for 12h;	A mixture of methyl 5-amino-l-benzothiophene-2-carboxylate (100 rug, 0.480 mmol), acid chloride (83 muL, 0.63 mmol) and NMM (64 muL, 0.58 mmol) was stirred in 2: 1 THF/CH2C12 for 12 hours at room temperature. The reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3, the organic layer was washed with sat'd NaCl, dried (Na2SO4), concentrated and finally triturated with diethyl ether to provide an off-white solid of the desired amide intermediate. The residue was then dissolved in 2:1 THF/water (3 mL), treated with LiOH (68 mg, 1.62 mmol). After stirring for 12 h at room temperature, the reaction mixture was partitioned between CH2Cl2 and 2M citric acid, the organic layer was washed with sat'd NaCl, dried (Na2SO4) and concentrated to a white solid and afforded 53 mg (42% yield, without purification) of the desired acid intermediate. The residue was dissolved in DMF (2 mL) and treated with EDC (49 mg, 0.26 mmol), HOBt (35 mg, 0.26 mmol) and 1,2-phenylenediamine (46 mg, 0.43 mmol). After stirring for 12 EPO <DP n="75"/>h, the reaction mixture was partitioned between EtOAc and sat'd NaHCO3, the organic layer was dried (Na2SO4), concentrated and finally triturated with diethyl ether to provide the desired product: 1H NMR (600 MHz, DMSO-J5) delta 10.34 (s, 1 H), 9.85 (s, 1 H), 8.33 (s, 1 H), 8.21 (s, 1 H), 7.93 (d, J = 8.4 Hz, 1 H), 7.53 (d, J = 9.0 Hz, 1 H), 7.32 (m, 4 H), 7.23 {I, J = 1.2 Hz, 1 H), 7.13 (d, J = 7.8 Hz, 1 H), 6.94 (t, J = 7.8 Hz, 1 H), 6.75 (d, / = 7.8, Hz, 1 H), 6.57 (t, J = 7.8, Hz, 1 H), 4.95 (s, 2 H), 3.66 (s, 2 H); MS: cal'd 402 (MH+), exp 402 (MH+).

Reference： [1]Patent: WO2006/101454,2006,A1 .Location in patent: Page/Page column 1.3
[2]Patent: WO2006/115845,2006,A1 .Location in patent: Page/Page column 73-74

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Code	Phrase
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Code	Phrase
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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

[ CAS No. 20699-85-8 ] {[proInfo.proName]}

Quality Control of [ 20699-85-8 ]

Related Doc. of [ 20699-85-8 ]

Product Details of [ 20699-85-8 ]

Calculated chemistry of [ 20699-85-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 20699-85-8 ]

Application In Synthesis of [ 20699-85-8 ]

[ 20699-85-8 ] Synthesis Path-Upstream 1~4

[ 20699-85-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 20699-85-8 ]

Esters

Amines

Related Parent Nucleus of [ 20699-85-8 ]

Benzothiophenes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 20699-85-8 ]

Related Parent Nucleus of
[ 20699-85-8 ]