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CAS No. : | 101767-28-6 | MDL No. : | MFCD00662677 |
Formula : | C5H7N3OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ONAWFUIPKRAZKL-UHFFFAOYSA-N |
M.W : | 157.19 | Pubchem ID : | 2744058 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 37.98 |
TPSA : | 96.25 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.1 cm/s |
Log Po/w (iLOGP) : | 1.46 |
Log Po/w (XLOGP3) : | 0.22 |
Log Po/w (WLOGP) : | 0.06 |
Log Po/w (MLOGP) : | -0.8 |
Log Po/w (SILICOS-IT) : | 0.91 |
Consensus Log Po/w : | 0.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.19 |
Solubility : | 10.1 mg/ml ; 0.0644 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.8 |
Solubility : | 2.49 mg/ml ; 0.0158 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.31 |
Solubility : | 7.72 mg/ml ; 0.0491 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
92% | With potassium hydroxide In ethanol for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With hydrazine hydrate In methanol at 60℃; for 1h; | |
64% | With hydrazine hydrate In ethanol for 14h; Reflux; | C.8; J.31 General procedure: In a 100 mL round-bottom flask equipped with a condenser, ethyl 2-methylthiazole-4-carboxylate 2.2a (10 g, 58.4 mmol, 1 eq.) was dissolved in anhydrous EtOH (25 mL) and treated at RT with hydrazine monohydrate (17.0 mL, 354.4 mmol, 6 eq.). The resulting yellow solution was heated at reflux temperature for 14 h. After allowing the reaction mixture to come to RT, the solution was concentrated under reduced pressure to afford 13.4 g of a brown oil. Co-evaporations using 3 x 200 mL of a mixture of commercial anhydrous DCM:MeOH (1: 1) were performed to remove residual water. The residue was then recrystallized from hot EtOH (60 mL). The obtained crystals were filtered and washed with cooled (0 °C) EtOH (2 x 30 mL). The orange solid was dried under vacuum for 1 h to afford 2a. Yield: 5.85 g, 64 %. LCMS: P = 100 %, retention time = 0.5 min, (M+H)+: 158; 1H-NMR (CDC13): δ 8.32 (br, 1H), 7.96 (s, 1H), 4.07 (br, 2H), 2.70 (s, 3H). |
64% | With hydrazine hydrate In ethanol at 20℃; for 14h; Inert atmosphere; |
48% | With hydrazine hydrate In ethanol at 90℃; for 16h; | 9.1 To a solution of ethyl 2-methylthiazole-4-carboxylate (5.0 g, 29.2 mmol) in ethanol (50 mL) was added hydrazine hydrate (16.5 g, 280.4 mmol) at 20 °C. Then the reaction was stirred at 90 °C for 16 hours and concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 10% methanol in dichlorom ethane) to afford 2-methylthiazole-4-carbohydrazide (2.2 g, 48%) as a yellow solid. LCMS RT = 0.483 min, m/z = 158.2 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / KOH / ethanol / 0.5 h 2: 48 percent / H2SO4 (conc.) / 0.08 h / 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 92 percent / KOH / ethanol / 0.5 h 2: 48 percent / H2SO4 (conc.) / 0.08 h / 5 °C 3: 68 percent / 10 M NaOH (aq) / H2O / 0.33 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 92 percent / KOH / ethanol / 0.5 h 2: 48 percent / H2SO4 (conc.) / 0.08 h / 5 °C 3: 83 percent / 10 M NaOH (aq) / H2O / 0.33 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: ethanol / Reflux; Inert atmosphere 2.1: hydrogenchloride / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: ethanol / Reflux 2: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 1.5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: hydrogenchloride / isopropyl alcohol / 0.67 h / 0 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: ethanol / 6 h / 70 °C 2: hydrogenchloride / 1,4-dioxane / 6 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: hydrogenchloride / isopropyl alcohol / 0.67 h / 0 °C / Inert atmosphere 4.1: 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4.2: 0.17 h / 0 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: ethanol / 6 h / 70 °C 2: hydrogenchloride / 1,4-dioxane / 6 h / 100 °C 3: 4-methyl-morpholine / dichloromethane / 0.17 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol Reflux; | D.17.1 Step 1: Synthesis of iert-butyl 8-methyl-3-(2-methylthiazol-4-yl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate3.1a Step 1: Synthesis of iert-butyl 8-methyl-3-(2-methylthiazol-4-yl)-5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate3.1aIn a 100 mL round-bottom flask equipped with a condenser, imino-ether lb (1.089 g, 4.77 mmol, 1 eq.) was dissolved in commercial anhydrous EtOH (20 mL), to which was added 2-methylthiazole-4-carbohydrazide 2a (750 mg, 4.77 mmol, 1 eq.) in one portion. The resulting solution was stirred under reflux overnight. The reaction mixture was cooled down to RT and the solvent was removed under reduced pressure. The crude compound was then purified on silica gel (DCM/MeOH: 99/1 to 98/2) to afford the desired product 3.1a as white solid (1.07 g, 3.33 mmol, 70%). LCMS: P = 100 %, retention time = 2.1 min, (M+H)+: 321. |
70% | In ethanol Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol at 60 - 70℃; for 8h; Inert atmosphere; | |
65% | In ethanol at 70℃; for 6h; | K.32 Scheme 32: Synthesis of (R)-4-(7-(2,4-dimethoxybenzyl)-8-methyl-5,6,7,8-tetrahydro- [l,2,4]triazolo[4,3-a]pyrazin-3-yl)-2-methylthiazole(/i)-F.a General procedure: Scheme 32: Synthesis of (R)-4-(7-(2,4-dimethoxybenzyl)-8-methyl-5,6,7,8-tetrahydro- [l,2,4]triazolo[4,3-a]pyrazin-3-yl)-2-methylthiazole(/i)-F.aIna50 mL round-bottom flask equipped with a condenser, imino-ether (R)-D (4.5 lg, 14.96mmol, 1 eq.) was dissolved in anhydrous EtOH (15mL), to which was added 2-methylthiazole-4-carbohydrazideE.a (2.35g, 14.96mmol, 1 eq.) in one portion. The resulting solution was stirred at 70 °C for 6 hours. The reaction mixture was cooled down to RT and the solvent was removed under reduced pressure. The crude compound was then purified by silica gel chromatography (DCM/MeOH: 99/1 to 95/5) to afford the desired product (R)-F.a as pale yellow foamy solid. Yield: 3.78 g, 65 %. LCMS: P = 96 , retention time = 1.8 min, (M+H)+: 386; chiral HPLC retention time = 13.9 min, ee = 95 ; 1H-NMR (CDC13): δ 7.85 (s, 1H), 7.19 (s, 1H), 6.41 (m, 2H), 4.38 (m, 1H), 4.16 (m, 1H), 3.96 (m, 1H), 3.86 (d, JAB= 15.0, 1H), 3.74 (s, 3H), 3.73 (s, 3H), 3.56 (d, JAB= 15.0, 1H), 3.11 (m, 1H), 2.66 (s, 3H), 2.62 (m, 1H), 1.64 (d, J = 6.6, 3H); 13C-NMR (CDC13): δ 166.2, 160.2, 158.8, 154.6, 148.1, 143.1, 130.9, 118.8, 118.2, 104.2, 98.5, 77.6, 77.2, 76.8, 70.4, 70.2, 55.4, 55.4, 55.8, 50.2, 45.8, 44.2, 19.2, 17.7, 15.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In methanol at 60 - 70℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0.17 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0.17 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: ethanol / Reflux; Inert atmosphere 2.1: hydrogenchloride / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: 4-methyl-morpholine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0.17 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 8 h / 60 - 70 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With saccharin In methanol at 20℃; for 0.5h; Green chemistry; | Saccharin-mediated Paal-Knorr pyrrole cyclocondensation(General method). General procedure: Saccharin (0.183 g, 1.0 mmol)was added to a solution of hexane-2,5-dione (1) (0.684 g,6.0 mmol) and hydrazide 2a-l (4.0 mmol) in methanol(6 ml). The mixture was stirred at room temperature for30 min. After the completion of the reaction, the mixturewas cooled in an ice bath. The brown solid product wasfiltered off and recrystallized from MeOH. The filtratecould be used for the next two runs with fresh reactants 1and 2a-l without any sign of decreased catalytic activity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene Heating; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / Heating; Inert atmosphere 2: potassium hydroxide / ethanol; water / 20 h / Heating; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: toluene / Heating; Inert atmosphere 2: potassium hydroxide / ethanol; water / 20 h / Heating; Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: toluene / Heating; Inert atmosphere 2: potassium hydroxide / ethanol; water / 20 h / Heating; Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 4: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h; | 9.2 To a solution of 2-methylthiazole-4-carbohydrazide (2.0 g, 12.7 mmol) and N,N- Diisopropylethylamine (1.6 g, 12.7 mmol) in tetrahydrofuran (20 mL) was added (2,2- difluoroacetyl) 2,2-difluoroacetate (2.7 g, 15.3 mmol). The reaction was stirred at 20 °C for 16 hours and concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 5% methanol in dichloromethane) to afford N'- (2,2-difluoroacetyl)-2-methyl-thiazole-4-carbohydrazide (2.8 g, 94%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C 2: Burgess Reagent / tetrahydrofuran / 3 h / 90 °C / Microwave irradiation 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 80 °C 4: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C 2: Burgess Reagent / tetrahydrofuran / 3 h / 90 °C / Microwave irradiation 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C 2: Burgess Reagent / tetrahydrofuran / 3 h / 90 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C 2: Burgess Reagent / tetrahydrofuran / 3 h / 90 °C / Microwave irradiation 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 80 °C 4: potassium carbonate / N,N-dimethyl-formamide / 1 h / 30 °C |
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