5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 25 - 50℃; for 1h; | 99% |
With hydrogenchloride In ethanol at 45℃; Solvent; Inert atmosphere; | 76% |
With hydrogenchloride; water In acetone at 56℃; for 3h; |
5-trityl-4,5,6,7-tetrahydro-tieno[3,2-c]pyridine
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine With N,N,N,N,-tetramethylethylenediamine; n-hexyllithium In toluene at 0℃; Large scale; Stage #2: With boric acid tributyl ester In toluene at 0℃; for 1h; Large scale; Further stages; | 86.1% |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 1.2: 1 h / 0 - 15 °C / Inert atmosphere 1.3: 2 h / 0 - 30 °C 2.1: hydrogenchloride; water / acetone / 3 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 1.2: -5 - 10 °C 2.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 1.2: 1 h / 0 - 15 °C 1.3: 1.75 h / 0 - 30 °C / Reflux 2.1: hydrogenchloride / acetone / 4.5 h / 25 - 30 °C / Reflux View Scheme |
6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 9 h / 0 - 5 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 2.2: 1 h / 0 - 15 °C / Inert atmosphere 2.3: 2 h / 0 - 30 °C 3.1: hydrogenchloride; water / acetone / 3 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12 - 28 °C 2.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 2.2: -5 - 10 °C 3.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 9 h / 0 - 5 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 15 °C / Inert atmosphere 2.2: 1 h / 0 - 15 °C 2.3: 1.75 h / 0 - 30 °C / Reflux 3.1: hydrogenchloride / acetone / 4.5 h / 25 - 30 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate / 1,4-dioxane / 0.5 h / 80 °C 1.2: 1 h 2.1: copper dichloride / methanol / 4 h 3.1: methanol / 24 h / Inert atmosphere; Reflux 4.1: hydrogenchloride / methanol / 12 h / 20 °C View Scheme |
[2-(2-thyenyl)ethyl]amine
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dichloromethane / 40 - 45 °C 1.2: 20 - 70 °C 2.1: triethylamine / dichloromethane / 12 - 28 °C 3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -5 - 10 °C 3.2: -5 - 10 °C 4.1: hydrogenchloride / water; acetone / 1 h / 25 - 50 °C View Scheme |
6,7-dihydro-4H-thieno[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: copper dichloride / methanol / 4 h 2: methanol / 24 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol / 12 h / 20 °C View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 12h; | 6.5 g |
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
Conditions | Yield |
---|---|
With ammonium bicarbonate In dichloromethane at 5 - 20℃; | 98% |
With copper(l) iodide; sodium carbonate; XPhos In 1,4-dioxane at 60℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere; | 90.2% |
With potassium phosphate; iodine In 1,4-dioxane at 80℃; for 4h; Temperature; Time; Reagent/catalyst; | 87.6% |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
2-Oxoclopidogrel
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; | 70% |
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; | 70% |
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With water; potassium carbonate In dichloromethane for 0.166667h; Stage #2: (R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester In dichloromethane for 6h; Reflux; | |
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; | 18.1 g |
With potassium carbonate In acetonitrile at 25 - 35℃; for 12h; | 25.4 g |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; | 70% |
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; | 70% |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
methyl 2-bromo-2-(2-chlorophenyl)acetate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; | 62% |
With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 2h; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
2-bromo-2-cyclopropyl-1-phenylethan-1-one
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 10 - 15℃; | 60% |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
A
(S)-(2-chlorophenyl)(2-hydroxy-6,7-dihydro-4H-thiophene[3,2-c]pyridin-5-yl)acetic acid methyl ester
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile for 15h; Inert atmosphere; | A 54% B n/a |
α-cyclopropylcarbonyl-2-fluorobenzyl chloride
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile at 60℃; for 12h; Inert atmosphere; | 52% |
With sodium carbonate In acetonitrile at 60℃; for 12h; Molecular sieve; Inert atmosphere; | 50% |
methyl 2-chloro-2-(2-chlorophenyl)acetate
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 55℃; for 0.05h; Inert atmosphere; Stage #2: methyl 2-chloro-2-(2-chlorophenyl)acetate In N,N-dimethyl-formamide at 55℃; for 0.166667h; Inert atmosphere; | 44% |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
acetic anhydride
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 5℃; for 1h; Inert atmosphere; | 20.03% |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
2,4-dihydroxy-5- isopropylbenzoic acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 4h; | 10% |
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
acetic anhydride
prasugel
Conditions | Yield |
---|---|
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 6h; Stage #3: acetic anhydride With triethylamine In acetonitrile at 0 - 30℃; for 6.5h; | |
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50 - 55℃; for 2h; Stage #2: acetic anhydride In N,N-dimethyl-formamide at 10 - 45℃; |
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 7h; Stage #3: With hydrogenchloride In ethyl acetate; acetone at 25 - 30℃; for 1h; | |
Stage #1: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetone; acetonitrile at 25 - 30℃; for 7.5h; Stage #2: With hydrogenchloride In ethyl acetate; acetone at 25 - 30℃; for 1h; |
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 6.5 h / 0 - 30 °C 2.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
prasugel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C 3.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 3.2: 6 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 0 - 30 °C 2.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 2.2: 6 h / 0 - 5 °C View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 3.33 h / 10 - 30 °C 3.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C 3.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 3.2: 6 h / 0 - 5 °C 4.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 25 - 55 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 6 h / 25 - 30 °C 1.3: 0 - 30 °C 2.1: triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 2.2: 6 h / 0 - 5 °C 3.1: hydrogenchloride / ethyl acetate; acetone / 0.75 h / 0 - 5 °C View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 25 - 30 °C 1.2: 7 h / 25 - 30 °C 2.1: hydrogen bromide / water; acetone / 1 h / 0 - 5 °C 3.1: ammonia / dichloromethane; water / 0 - 30 °C 3.2: 1 h / 25 - 30 °C View Scheme |
2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide
Conditions | Yield |
---|---|
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile at 25 - 30℃; for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 25 - 30℃; for 6h; Stage #3: With hydrogen bromide In water; acetone at 0 - 30℃; | |
Stage #1: 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride With potassium carbonate In acetonitrile for 0.5h; Stage #2: 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone In acetonitrile at 10 - 15℃; for 2.5h; Stage #3: With hydrogen bromide In water; acetone at 0 - 30℃; for 3h; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 20 °C / Inert atmosphere 3: hydrogenchloride; water / ethyl acetate / 20 °C View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 20 °C / Inert atmosphere View Scheme |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 28 - 30℃; for 1.75h; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
(R)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; for 26h; Inert atmosphere; |
5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride
methyl 2-phenyl-2-(((p-nitrophenyl)sulfonyl)oxy)acetate
Methyl alpha-(2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetonitrile at 20℃; |
Following is the structure of Thieno[3,2-c]pyridin-2(4H)-one,5,6,7,7a-tetrahydro-, hydrochloride (1:1) (CAS NO.115473-15-9):
Empirical Formula: C7H10ClNOS
Molecular Weight: 191.6784
Melting point: 2100 °C
Flash Point: 174.1 °C
Enthalpy of Vaporization: 62.25 kJ/mol
Boiling Point: 364.3 °C at 760 mmHg
Vapour Pressure: 1.17E-05 mmHg at 25 °C
Appearance of Thieno[3,2-c]pyridin-2(4H)-one,5,6,7,7a-tetrahydro-, hydrochloride (1:1) (CAS NO.115473-15-9): Cream Solid
Product Categories of Thieno[3,2-c]pyridin-2(4H)-one,5,6,7,7a-tetrahydro-, hydrochloride (1:1) (CAS NO.115473-15-9): Heterocyclic Compounds; Heterocycles; Sulfur & Selenium Compounds
SMILES: Cl.O=C1/C=C2/CNCCC2S1
InChI: InChI=1/C7H9NOS.ClH/c9-7-3-5-4-8-2-1-6(5)10-7;/h3,6,8H,1-2,4H2;1H
InChIKey: PUQKTVAKLPDUAW-UHFFFAOYAV
Thieno[3,2-c]pyridin-2(4H)-one,5,6,7,7a-tetrahydro-, hydrochloride (1:1) , its cas register number 115473-15-9. It also can be called 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridine-2(4H)-one hydrochloride .
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