[ CAS No. 98800-10-3 ]

Name: 98800-10-3|Methyl thieno[3,2-b]thiophene-2-carboxylate|98%
Brand: Ambeed
SKU: A145881
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Quality Control of [ 98800-10-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 98800-10-3 ]

CAS No. :	98800-10-3	MDL No. :	MFCD01934498
Formula :	C₈H₆O₂S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	198.26 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 98800-10-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	8
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.98
TPSA :	82.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.38
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	2.75
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	4.14
Consensus Log Po/w :	2.82

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.26
Solubility :	0.11 mg/ml ; 0.000553 mol/l
Class :	Soluble
Log S (Ali) :	-4.3
Solubility :	0.00996 mg/ml ; 0.0000502 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.403 mg/ml ; 0.00203 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.48

Safety of [ 98800-10-3 ]

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 [ 98800-10-3 ]

* 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 [ 98800-10-3 ]
Downstream synthetic route of [ 98800-10-3 ]

[ 98800-10-3 ] Synthesis Path-Upstream 1~1

1
[ 98800-10-3 ]
[ 31486-86-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273

[ 98800-10-3 ] Synthesis Path-Downstream 1~32

1
[ 186581-53-3 ]
[ 1723-27-9 ]
[ 98800-10-3 ]

Reference： [1]Journal of the Institute of Petroleum,1951,vol. 37,p. 396,401

2
[ 1723-29-1 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In dimethyl sulfoxide; ethyl acetate	Thieno[3,2-b]thiophene-2-carboxamidine hydrochloride Methyl 2-(2-formylthien-3-ylthio)ethanoate (47.8 mg, 0.22 mmol) and triethylamine (0.20 g, 2 mmol) were heated in DMSO (2 mL) under N2 with stirring for 2 h. The reaction mixture was diluted with ether (30 mL), and was washed with dilute HCl (1M, 10 mL), water (2*10 mL), and saturated brine (10 mL), and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by preparative tlc on silica (10% EtOAc in hexanes) to give methyl thieno[3,2-b]thiophene-2-carboxylate (36.2 mg, 83%) as a crystalline solid mp 96°-7° C.
36.93 g	With piperidine; acetic acid In benzene for 5h; Heating;

Reference： [1]Current Patent Assignee: EISAI CO LTD - US5340833, 1994, A
[2]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

3
[ 67-56-1 ]
[ 1723-27-9 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuric acid; In water; at 0℃; for 8h;Reflux;	500 mg (2.7 mmol, 1.0 eq) of <strong>[1723-27-9]thieno [3,2-B] thiophene-2-carboxylic acid</strong> (Compound 12-1) was added to methanol 5.0 ml, cooled to 0 C,Concentrated sulfuric acid (265 mg, 2.7 mmol, l.Oeq)After the addition was complete, the reaction was warmed to room temperature and then heated to reflux overnight.TLC raw materials are surplus,The reaction was cooled to 0 C,Supplemented with concentrated sulfuric acid (530 mg, 5.4 mmol, 2.0 eq)Then heated to reflux for 8 hours, TLC reaction completely.The reaction solution was cooled to room temperature, poured into about 50 ml of ice water, stirred for 20 minutes, filtered and the filter cake was rinsed with water and dried to give the product as yellowish solid compound 12-2 (504 mg, yield 94%Directly for the next reaction.

Reference： [1]Patent: CN105399697,2016,A .Location in patent: Paragraph 0236; 0237
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 2697 - 2717
[3]Journal of medicinal chemistry,1985,vol. 28,p. 1896 - 1903

4
[ 98800-10-3 ]
[ 33577-16-1 ]
[ 98800-11-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature;

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

5
[ 98800-10-3 ]
[ 127025-34-7 ]

Yield	Reaction Conditions	Operation in experiment
90.8%	With lithium aluminium tetrahydride In tetrahydrofuran at -30 - 20℃; for 1h; Inert atmosphere;	12 Lithium aluminium hydride (474 mg, 12.48 mmol, 1.5 eq)Was suspended in dry THF (5.0 ml), protected with nitrogen,To a solution of 1.65 g (8.32 mmol, 1. Oeq) of thieno [3,2-B] thiophene-2-carboxylate in THF (10 ml) was cooled to -30 ° C., Slowly dropwise added to the reaction solution, after dropping slowly warming to room temperature for 1 hour, TLC reaction completely. After the reaction was cooled to -20 ° C, EA was slowly added dropwise to produce no bubbles, then 20% aqueous solution of sodium hydroxide was added dropwise to form a loose precipitate; the filter cake was rinsed well with EA; the filtrate was saturated with chlorinated Ammonium chloride solution 2 times, washed 1 times, brine washed 1 times, anhydrous sodium sulfate drying, filtration, the filtrate was concentrated to dry in crude.15 ml of n-hexane was added to the crude product and the mixture was beaten for 30 minutes. The filter cake was concentrated under reduced pressure to give compound 12-3, 1.29 g, yield 90.8%.
90%	With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 5h;
77.6%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	6B; XIII Example 6-B Under nitrogen, compound 3 (300 g, 1.52 mol) dissolved in anhydrous THF (2500 mL) was added dropwise to a mixture of LiAlH4 (75 g, 1.98 mol) in anhydrous THF (1500 mL) at 0° C. After the addition, the mixture was stirred at rt for 2 hs and compound 3 was consumed completely. Cooled to 0° C., water (75 mL) was added dropwise followed by the addition of 10% NaOH aq. (125 mL) dropwise. The mixture was filtered and the cake was washed with DCM several times. The filtration was concentrated under reduced pressure to give compound 4 (258 g, 77.6%) as a white solid.

With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature; Yield given;

Reference： [1]Current Patent Assignee: TOPHARMAN SHANGHAI CO., LTD.; CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES; Shanghai Institute of Materia Medica (in: CAS) - CN105399697, 2016, A Location in patent: Paragraph 0236; 0238
[2]Manuela; Raposo; Herbivo, Cyril; Hugues, Vincent; Clermont, Guillaume; Castro, M. Cidália R.; Comel, Alain; Blanchard-Desce, Mireille [European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273]
[3]Current Patent Assignee: ROCHE HOLDING AG - US2014/200215, 2014, A1 Location in patent: Paragraph 1015; 1017
[4]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

6
[ 98-03-3 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 92.5 percent / NaOAc / acetic acid / 0.5 h / Heating 2: 93 g / 8 percent NaOH / 0.5 h / 45 - 60 °C 3: Cl₂ / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 4: 400 g / HCl / 2 h / Heating

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

7
[ 98800-10-3 ]
[ 98800-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

8
[ 98800-10-3 ]
[ 98800-12-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

9
[ 98800-10-3 ]
[ 104235-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

10
[ 98800-10-3 ]
[ 104235-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

11
[ 98800-10-3 ]
[ 104235-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

12
[ 98800-10-3 ]
[ 104320-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C 7: 50 percent HCOOH, zinc / methanol / 2 h / 0 °C

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

13
[ 98800-10-3 ]
[ 104320-41-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO₄ / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C 7: 50 percent HCOOH, zinc / methanol / 2 h / 0 °C

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

14
5-(2'-thiophenemethylene)rhodamine [ No CAS ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 93 g / 8 percent NaOH / 0.5 h / 45 - 60 °C 2: Cl₂ / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 3: 400 g / HCl / 2 h / Heating

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

15
3-(2-thienyl)-2-sulfanylpropenoic acid [ No CAS ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Cl₂ / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 2: 400 g / HCl / 2 h / Heating

Reference： [1]Kukolja; Draheim; Graves; Hunden; Pfeil; Cooper; Ott; Counter [Journal of medicinal chemistry, 1985, vol. 28, # 12, p. 1896 - 1903]

16
[ 930-96-1 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 17.6 g / pyridinium tosylate / toluene / 1 h / Heating 3: p-toluenesulfonic acid hydrate / acetone / 1 h 4: 36.93 g / piperidine, acetic acid / benzene / 5 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

17
[ 56857-02-4 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: p-toluenesulfonic acid hydrate / acetone / 1 h 3: 36.93 g / piperidine, acetic acid / benzene / 5 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

18
[ 98800-10-3 ]
[ 31486-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C
	Multi-step reaction with 3 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]
[2]Manuela; Raposo; Herbivo, Cyril; Hugues, Vincent; Clermont, Guillaume; Castro, M. Cidália R.; Comel, Alain; Blanchard-Desce, Mireille [European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273]
[3]Podlesný, Jan; Pytela, Oldřich; Klikar, Milan; Jelínková, Veronika; Kityk, Iwan V.; Ozga, Katarzyna; Jedryka, Jaroslaw; Rudysh, Myron; Bureš, Filip [Organic and Biomolecular Chemistry, 2019, vol. 17, # 14, p. 3623 - 3634]

19
[ 98800-10-3 ]
[ 127025-35-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

20
[ 98800-10-3 ]
[ 127025-38-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

21
[ 98800-10-3 ]
5-[(E)-Methyliminomethyl]-thieno[3,2-b]thiophene-2-sulfonic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

22
[ 98800-10-3 ]
[ 127025-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

23
[ 98800-10-3 ]
5-[(E)-2-Methoxy-ethylimino]-methyl}-thieno[3,2-b]thiophene-2-sulfonic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

24
[ 98800-10-3 ]
[ 127025-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

25
[ 98800-10-3 ]
[ 127025-36-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

26
[ 98800-10-3 ]
Bis-(2-methoxy-ethyl)-(5-sulfamoyl-thieno[3,2-b]thiophen-2-ylmethylene)-ammonium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: LiAlH₄ / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH₄OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d

Reference： [1]Prugh; Hartman; Mallorga; McKeever; Michelson; Murcko; Schwam; Smith; Sondey; Springer; Sugrue [Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818]

27
[ 110-89-4 ]
[ 1723-29-1 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; acetic acid In water; toluene; benzene	1.E Methyl thieno[3,2-b]thiophene-2-carboxylate (6) STR9 Step E Methyl thieno[3,2-b]thiophene-2-carboxylate (6) STR9 Piperidine (37.9 g., 445 mmoles) was added to a solution of acetic acid (26.7 g., 445 mmole) in benzene (1 L) and stirred for 5 minutes. Methyl 2-formylthiophen-3-yl-3-thiapropionate (5) (96.91 g., 448 mmoles) was added in benzene to a total volume of benzene (2.2 L). The solution was refluxed while stirring and water was collected via a Dean-Stark trap. After 5 hours of reflux, 7.8 ml of water was collected. The mixture was cooled to room temperature and extracted with water two times, then 1N.HCl followed by water, and then by a saturated solution of sodium bicarbonate two times. The resulting benzene solution was dried (MgSO4), filtered and evaporated to leave 88 g. of crude product. This was extracted with room temperature ether, then three times with boiling ether, leaving a tarry gum. Silica gel (100 g.) was added to the ether solution of the product. The solvent was evaporated and the clumps broken up leaving a free flowing product adsorbed on silica gel. This was chromatographed on silica gel eluding with 50% hexane in toluene. The solvent was evaporated from the fractions containing the product and after trituration with hexane, 36.93 g. of methyl thieno[3,2-b]thiophene-2-carboxylate (6), mp 96°-97° C. was isolated. Calc. for C8 H6 O2 S2: C, 48.47; H, 3.05; Found: C, 48.85; H, 3.14.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US4876271, 1989, A

28
[ 108-89-4 ]
[ 98800-10-3 ]
[ 4637-24-5 ]
[ 1313384-17-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: picoline; methyl thieno<3,2-b>thiophene-2-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water Stage #3: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal	4-[3-(3-Thieno[3,2-b]thiophen-2-yl)-lH-pyrazol-4-yl]pyridineTo a solution of 4-methylpyridine (1 eq, 22.6 mmol) and methyl 3-thieno[3,2-b]thiophene-2 carboxylate (1.12 eq, 25.3 mmol) in anhydrous tetrahydroiurane (20 mL) at 0 °C, under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in tetrahydrofurane, 2 eq, 45.1 mmol). The mixture was stirred 3 h at 5 °C and overnight at room temperature. The resulting precipitate was filtered, washed with diisopropylether and dried to afford a yellow solid (7.4g).This solid was dissolved in 150 mL of water and a 1M solution of hydrochloric acid was carefully added until pH reached 5. The resulting precipitated was filtered and dried to afford a green solid (5.3g). This solid was dissolved in Ν,Ν-dimethylformamide dimethylacetal (30 mL). The mixture was refluxed for 1 h. The solvant was evaporated. The residue was purified by colomn chromatography on silica gel (ethyl acetate) to afford 3.8 g of a brown solid.This solid was dissolved in 80 mL of absolute ethanol and hydrazine hydrate (17.2 mmol) and triethylamine (17.2 mmol) were added. The resulting mixture was stirred at reflux for 3 h. The solvant was then evaporated and the residue was suspended in 50 mL of ethanol. The resulting precipitate was filtered and dried to afford 2.8 g of 4-[3-(3-thieno[3,2-b]thiophen-2-yl)-lH-pyrazol- 4-yl]pyridine (44% yield).'H-NMR (400 MHz, dg-DMSO): δ = 13.42 (bs, 1H), 8.56 (d, 2H), 8.23 (s, 1H), 7.67 (d, 1H), 7.45 (m, 3H), 7.37 (s, lH) ppm

Reference： [1]Current Patent Assignee: BAYER AG - WO2011/76725, 2011, A1 Location in patent: Page/Page column 87

29
[ 930-96-1 ]
[ 2365-48-2 ]
[ 98800-10-3 ]

Yield	Reaction Conditions	Operation in experiment
82.6%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 5h;	To a mixture of compound 1 (350 g, 1.83 mol) and K2CO3 (1000 g, 7.33 mol) in DMF (4000 mL) was added compound 2 (195 g, 1.83 mol) at rt. The resultant mixture was stirred at 70 C. for 5 hs. After cooled to rt, the mixture was poured into ice-water and solids were precipitated out which was obtained by filtration and dried in vacuo at 50 C. to give compound 3 (300 g, 82.6%) as a white solid.

Reference： [1]Patent: US2014/200215,2014,A1 .Location in patent: Paragraph 1015; 1016
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3623 - 3634
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5263 - 5273

30
[ 98800-10-3 ]
methyl 5-iodothieno[3,2-b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With iodine; bis-[(trifluoroacetoxy)iodo]benzene In tetrachloromethane at 20℃;

Reference： [1]Li, He; Huang, Qi; Chen, Cheng; Xu, Bin; Wang, He-Yao; Long, Ya-Qiu [Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2697 - 2717]

31
[ 98800-10-3 ]
[ 1723-27-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3623 - 3634

32
[ 98800-10-3 ]
methyl 3-iodothieno[3,2-b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl thieno<3,2-b>thiophene-2-carboxylate With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran; toluene at -60℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at -60 - 20℃;	3-Iodothieno[3,2-b]thiophene-2-carboxylic acid 3-Iodothieno[3,2-b]thiophene-2-carboxylic acid Under an argon atmosphere, methyl thieno[3,2-b]thiophene-2-carboxylate (5.00 g, 25.2 mmol) was dissolved in 20 ml of dry tetrahydrofuran. The solution was cooled to -60° C. and tetramethylpiperidinemagnesium chloride lithium chloride complex (6.11 g, 25.2 mmol, dissolved 1M in toluene/tetrahydrofuran) was slowly added dropwise. After 1 h of stirring at -60° C., iodine (6.40 g, 25.2 mmol, dissolved in 10 ml of tetrahydrofuran) was added dropwise. The mixture was slowly warmed to room temperature and 200 ml of saturated ammonium chloride solution were added. The organic phase was separated off, the solvent was removed on a rotary evaporator and the crude product methyl 3-iodothieno[3,2-b]thiophene-2-carboxylate was used directly for the subsequent reaction. Methyl 3-iodothieno[3,2-b]thiophene-2-carboxylate (8.1 g, 25 mmol) was dissolved in 100 ml of THF, and lithium hydroxide (2.99 g, 125 mmol) in 20 ml of water was added. The reaction mixture was stirred vigorously at room temperature for 12 h. The mixture was neutralized with 1N hydrochloric acid, and water was added. A precipitate (3-iodothieno[3,2-b]thiophene-2-carboxylic acid) formed, which was isolated by filtration.

Reference： [1]Current Patent Assignee: BAYER AG - US2020/128830, 2020, A1 Location in patent: Paragraph 0521-0523

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[ CAS No. 98800-10-3 ]

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[ 98800-10-3 ] Synthesis Path-Upstream 1~1

[ 98800-10-3 ] Synthesis Path-Downstream 1~32

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Esters

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