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CAS No. : | 104680-25-3 | MDL No. : | MFCD08059079 |
Formula : | C10H13NO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 243.28 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 60.9 |
TPSA : | 106.86 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.19 cm/s |
Log Po/w (iLOGP) : | 2.43 |
Log Po/w (XLOGP3) : | 2.24 |
Log Po/w (WLOGP) : | 1.69 |
Log Po/w (MLOGP) : | 0.91 |
Log Po/w (SILICOS-IT) : | 2.31 |
Consensus Log Po/w : | 1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.59 |
Solubility : | 0.618 mg/ml ; 0.00254 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.12 |
Solubility : | 0.0185 mg/ml ; 0.0000759 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.28 |
Solubility : | 1.29 mg/ml ; 0.00528 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tin(ll) chloride; sodium nitrite 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: bis(trichloromethyl) carbonate; 2-amine-thiophene-3,4-dicarboxylic acid ethyl ester With triethylamine In tetrahydrofuran; dichloromethane at 0℃; for 1h; Stage #2: 3-[1-(1,2,3,4-tetrahydro)quinolinyl]sulfonylaniline In tetrahydrofuran; dichloromethane at 20℃; Stage #3: With sodium ethanolate In ethanol at 60℃; for 2h; | 32 Ethyl 3-[3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate Example 32 Ethyl 3-[3-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate To a solution of diethyl 2-aminothiophene-3,4-dicarboxylate (100 mg), triethylamine (0.21 ml) in dichloromethane (3 ml), a solution of triphosgene (44.5 mg) in THF (1 ml) was added at 0°C, and the mixture was stirred under nitrogen atmosphere at 0°C for 1 hr. The insoluble material was removed by filtration. 3-(3,4-Dihydroquinolin-1(2H)-ylsulfonyl)aniline (118 mg) was added, and the mixture was stirred under nitrogen atmosphere at room temperature overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography, and dissolved in ethanol (7 ml). A 20% solution (140 mg) of sodium ethoxide in ethanol was added, and the mixture was stirred under nitrogen atmosphere at 60°C for 2 hr. After allowing to cool to room temperature, water-saturated brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, and crystallized from diisopropyl ether to give the object (69.7 mg) as crystals. 1H-NMR (DMSO-d6) δ 1.23 (3H, t), 1.58-1.69 (2H, m), 2.43-2.54 (2H, m), 3.72-3.79 (2H, m), 4.21 (2H, q), 7.04-7.10 (2H, m), 7.12-7.22 (1H, m), 7.47-7.63 (5H, m), 7.73 (1H, s), 12.46 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature 4: 43 percent / chlorine / CHCl3; CCl4 / 0.67 h / 10 - 15 °C 5: 74 percent / 1 N aq. sodium hydroxide / methanol / 1.5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature 3: 92 percent / 1 N sodium hydroxide / ethanol / 1 h / Ambient temperature 4: 43 percent / chlorine / CHCl3; CCl4 / 0.67 h / 10 - 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) sodium nitrite, conc. hydrochloric acid, 2.) stannous chloride, conc. hydrochloric acid / 1.) water, -10 to 5 deg C, 30 min, 2.) 5 deg C, 30 min 2: 91 percent / ethanol / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium borohydrid; sodium hydrogencarbonate In water; cyclopropanecarboxylic acid | 44.a a a Diethyl 2-[(cyclopropylmethyl)amino]-3,4-thiophenedicarboxylate Sodium borohydride (12.5 g) was added portionwise over 3 hours to a solution of diethyl 2-amino-3,4-thiophenedicarboxylate (25 g) in cyclopropanecarboxylic acid (125 ml). After a further 18 hours, further sodium borohydride (5 g) was added and the mixture heated at 50° C. for 18 hours. Further sodium borohydride (5 g) was added and the mixture stirred at 50° C. for 16 hours then at room temperature for 3 days. Water (500 ml) was added, the solution made alkaline by addition of sodium bicarbonate and extracted with ether (2*250 ml). Organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluding with ether/isohexane (2:3) to give the sub-title compound (12.1 g) as an oil. MS (+ve APCI) 298 ((M+H)+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: triethylamine; diphenyl phosphoryl azide 4.2: 0.42 h / 125 °C / Microwave irradiation | ||
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran 4.2: 0.42 h / 125 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C | ||
Multi-step reaction with 2 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C | ||
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C | ||
Multi-step reaction with 4 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C | ||
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C | ||
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C | ||
Multi-step reaction with 4 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C | ||
Multi-step reaction with 2 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane | ||
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C | ||
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: trifluoroacetic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / 20 °C | ||
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5: ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; N,N-dimethyl-formamide / 20 °C | ||
Multi-step reaction with 5 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: acetonitrile; dichloromethane 4: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ammonia; 4-(4-benzylpiperazin-1-yl)thieno[2,3-d]pyrimidin-2-amine / water; N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: methanol; sodium tetrahydroborate / tetrahydrofuran 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C 5.2: 20 °C | ||
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C 5.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: water; sodium hydroxide / methanol / 3 h / Reflux 4.1: triethylamine; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 5.2: 20 °C | ||
Multi-step reaction with 5 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: sodium hydroxide; water / methanol / 3 h / Reflux 4.1: triethylamine / N,N-dimethyl-formamide / 20 h / 20 °C 4.2: 1 h / 150 °C / Microwave irradiation 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 5.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 12 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfone / 0.75 h / 135 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3: triethylamine / dichloromethane / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: triethylamine / methanol / 0.5 h / 20 °C 3.2: 2 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: triethylamine / methanol / 0.5 h / 20 °C 3.2: 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 3 h | ||
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 2 h / 20 °C | ||
Multi-step reaction with 7 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / acetonitrile / 0.25 h / 20 °C 2.2: 3 h / 60 °C 3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 4 h / 80 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 20 °C 5.1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C 7.1: triethylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 7.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: water; sodium hydroxide / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C 6.1: potassium <i>tert</i>-butylate / dichloromethane / 2 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: dimethylsulfone / 0.75 h / 135 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / acetonitrile / 20 °C 3.1: acetonitrile; dichloromethane 4.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 12 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 16 h / 20 °C 6.1: potassium <i>tert</i>-butylate / dichloromethane / 2 h / 20 °C |
A1441348[ 1520161-91-4 ]
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