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CAS No. : | 31784-70-0 | MDL No. : | MFCD00219102 |
Formula : | C6H5N3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGWPHTRWLWDCOC-UHFFFAOYSA-N |
M.W : | 151.19 | Pubchem ID : | 592050 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P301+P310-P305+P351+P338 | UN#: | 2811 |
Hazard Statements: | H301-H319 | Packing Group: | Ⅲ |
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 |
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With sodium hydroxide; arsenic(III) trioxide at 140℃; |
Yield | Reaction Conditions | Operation in experiment |
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92% | With hydrogenchloride In water at 100℃; for 4h; Inert atmosphere; | 3.1 (1) Synthesis of S15 Add 3-amino-2-chloropyridine (1.0 mmol) to a 25 ml dry three-necked flask.The nitrogen was purged three times to bring the whole system to a nitrogen atmosphere, and concentrated hydrochloric acid (1.28 ml) was added.Further add potassium thionitrate (2.0 mmol), and heat the reaction system to 100 ° C for 4 h.The TLC tracks until the conversion of the raw materials is completed. After cooling, a saturated aqueous solution of sodium hydrogencarbonate was added and the mixture was adjusted to pH.A solid precipitated, and the filter cake was washed three times with water and dried to give a yellow solid S15 (yield: 92%). |
83% | With hydrogenchloride In water at 100℃; for 4h; Inert atmosphere; | 2.1 Step 1: Synthesis of Intermediate C A three-necked reactor equipped with a thermometer was charged with 9.00 g (70.01 mmol) of 3-amino-2-chloropyridine and 90 ml of concentrated hydrochloric acid under a nitrogen stream to prepare a homogeneous solution. After the addition of 10.21 g (105.01 mmol) of potassium thiocyanate to the solution, the mixture was stirred at 100° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to 20° C., followed by addition of 90 ml of water. The reaction mixture was added to 300 ml of a saturated sodium hydrogen carbonate aqueous solution while cooling the mixture with ice. The pH of the aqueous solution was adjusted to 8 by adding powdery sodium carbonate to precipitate crystals. The crystals were filtered off, washed with distilled water, and dried using a vacuum dryer to obtain 8.74 g of an intermediate C as a light yellow solid (yield: 83%). The structure of the target product was identified by 1H-NMR. 1H-NMR (500 MHz, DMSO-d6, TMS, δ ppm): 8.11 (dd, 1H, J=1.5 Hz, 5.0 Hz), 7.82 (s, 2H), 7.63 (dd, 1H, J=1.5 Hz, 8.0 Hz), 7.25 (dd, 1H, J=5.0 Hz, 8.0 Hz) |
59.9% | With hydrogenchloride In water at 100℃; for 4h; Inert atmosphere; | 1.1 Step 1: Synthesis of Intermediate A Example 1 Synthesis of Compound 1 Step 1: Synthesis of Intermediate A A four-necked reactor equipped with a thermometer was charged with 3.00 g (23.3 mmol) of 3-amino-2-chloropyridine and 30 ml of concentrated hydrochloric acid under a nitrogen stream to prepare a homogeneous solution. After the addition of 3.40 g (35.0 mmol) of potassium thiocyanate to the solution, the mixture was stirred at 100° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to 20° C., followed by addition of 30 ml of water. The resulting solution was added to 100 ml of a saturated sodium carbonate aqueous solution while cooling the solution with ice to precipitate a solid, which was filtered off. The solid was washed with water, and dried using a vacuum dryer to obtain 2.11 g of an intermediate A as a light yellow solid (yield: 59.9%). The structure of the target product was identified by 1H-NMR. 1H-NMR (500 MHz, DMSO-d6, TMS, δ ppm): 8.11 (dd, 1H, J=1.5 Hz, 5.0 Hz), 7.82 (s, 2H), 7.63 (dd, 1H, J=1.5 Hz, 8.0 Hz), 7.25 (dd, 1H, J=5.0 Hz, 8.0 Hz) |
With hydrogenchloride In ethanol for 66h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With acetic acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With hydrazine hydrate In methanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 18 percent / copper(II) bromide; tert-butyl nitrite / acetonitrile / 8 h / 20 - 60 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 2.2: tetrahydrofuran; hexane / 1 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 18 percent / copper(II) bromide; tert-butyl nitrite / acetonitrile / 8 h / 20 - 60 °C 2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 2.2: tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 1-hydroxybenzotriazole hydrate; N-methylmorpholine; 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 10 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Stage #1: 2-chloro-3-aminopyridine With hydrogenchloride; ammonium thiocyanate In ethanol; water at 85℃; for 72h; Stage #2: With ammonium hydroxide In chloroform; water | 1.2 Preparation 2: Synthesis of thiazolo[5,4-b]pyridin-2-ylamine A suspension of 2-chloro-3-aminopyridine (3 g, 23 [MMOLE),] and ammonium thiocyanate (3.5 g, 46.5 mmole) in 23 mL of ethanol was acidified with conc. HCI to [PH-1 (-1.] 8 mL). The reaction mixture was heated to [85 C] for 3 days. At this point, the solvent was evaporated and residual water was removed aziotropically by the distillation of 2-propanol. The yellow residue was mixed with 12 mL of 7 M ammonium hydroxide and 7 mL of chloroform. The solid was isolated by filtration to yield 1.50 g (43%) of the product as a white powder. MS [(M/Z,] ES+): 152 [(M+1,] [100%).] |
Multi-step reaction with 3 steps 1: NaNO2, hydrochloric acid / stannous chloride / H2O / 2 h / 0 °C 2: 82 percent 3: 61 percent / 80percent hydrazine hydrate / methanol / 2 h / Heating | ||
Multi-step reaction with 3 steps 1: acetone / 8 h / Reflux 2: sodium methylate / 1-methyl-pyrrolidin-2-one / 8 h / Reflux 3: sulfuric acid; water / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent 2: 61 percent / 80percent hydrazine hydrate / methanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; | 74 After adding 8.20 mg (0.054 mol) of 2-amino-thiazolo[5,4-b]-pyridine, 5.00 mg (0.037 mmol) of 1-hydroxybenzotriazole hydrate and 7.10 mg (0.037 mol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to a solution of the obtained carboxyl compound in N,N-dimethylformamide (1.2 ml), the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester = 1:1) to obtain the title compound as a white solid. The analysis data for the compound obtained in Production Example 74 are shown below.1HNMR(CDCl3)δ: 1.32(6H,d,J=6.0Hz), 4.54-4.62(1H,m), 7.32(1H,dd,J=4.6,8.2Hz), 7.37(1H,t,J=1.8Hz), 7.56(1H,t,J=1.8Hz), 7.74(1H,dd,J=1.4,8.2Hz), 7.79(1H,t,J=1.8Hz), 8.52(1H,dd,J=1.4,4.6Hz), 9.07(1H,s) ESI-MS(m/e): 430[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | 4-Chloro-6-iodo-quinazoline (1.00 g; 3.44 mmol) and 0.70 g (4.64 mmol) of thiazolo[5,4-b]pyridin-2-yl-amine were heated at 135C for 4 hours with stirring in 10 ml of phenol. Chloroform was added to the reaction solution followed by washing with a 1N aqueous solution of sodium hydroxide. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography (chloroform : methanol = 50:1) to give 486 mg (yield: 35%) of (6-iodo-qunazolin-4-yl)-thiazolo[5,4-b]pyridin-2-yl-amine as a yellow solid. To a solution of 80 mg (0.197 mmol) of the resulting iodine compound in 2 ml of N,N-dimethylacetamide were added 38 mg (0.197 mmol) of copper iodide, 128 mg (0.394 mmol) of cesium carbonate and 30 mg (0.295 mmol) of 3-mercapto-1,2,4-triazole followed by stirring at 140C for 5 hours. Water was added to the reaction solution followed by extracting with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a thin layer silica gel chromatography (chloroform : methanol = 8:1) to give 15 mg (yield: 20%) of the title compound as a yellow solid. 1 HNMR(CDCl3) δ: 7.43-7.46(1H,m),7.82(1H,d,J = 8.8Hz),7.90(1H,d,J = 8.8Hz),8.05(1H,d,J = 8.0Hz),8.18(1H,s),8.31(1H,s),8.43(1H,d,J = 3.6Hz),8.69(1H,s) ESI-MS(m/e):379[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With phenol at 140℃; for 2h; | 31 4,6-Dichloro-pyrido[3,2-d]pyrimidine (100 mg; 0.503 mmol) and 76 mg (0.503 mmol) of thiazolo[5,4-b]pyridin-2-yl-amine in 0.3 mol of phenol were heated at 140°C for 2 hours with stirring. Ethyl acetate was added to the reaction solution and the resulting solid was purified by a thin layer silica gel column chromatography (chloroform : methanol = 10:1) to give 78 mg (yield: 45%) of (6-chloro-pyrido[3,2-d]pyrimidin-4-yl)-thiazolo[5,4-b]pyridin-2-yl-amine as a yellow solid. DBU (18 mg; 0.120 mmol) and 12 mg (0.120 mmol) of 3-mercapto-1,2,4-triazole were added to a solution of 25 mg (0.080 mmol) of the resulting chloro compound in 1 ml of N,N-dimethylacetamide and the mixture was stirred at 140°C for 3 hours. The reaction solution was concentrated in vacuo and the resulting residue was purified by a reversed phase preparative HPLC (0.1 % TFA-containing water : acetonitrile = 90:10 → 10:90) to give 4 mg (yield: 13%) of the title compound as a yellow solid. 1 HNMR (CD3 OD) δ: 7.70 (1H, dd, J = 8.0, 4.8Hz), 7.81 (1H, d, J = 8.4Hz), 8.26 (1H, d, J = 8.4Hz), 8.35 (1H, dd, J = 8.0, 1.6Hz), 8.61-8.63 (2H, m), 9.07 (1H, s) ESI-MS(m/e):380[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | Stage #1: 2-aminothiazolo<5,4-b>pyridine; 4-chloro-6-(2-fluoro-1-fluoromethyl-ethoxy)-quinazoline With phenol at 140℃; for 2h; Stage #2: With sodium hydroxide In chloroform; water | 22 4-Chloro-6-hydroxy-quinazoline (500 mg; 2.78 mmol), 800 mg (8.33 mmol) of 1,3-difluoro-2-propanol and 2.18 g (8.33 mmol) of triphenyl phosphine were dissolved in 30 ml of THF and 3.62 g (8.33 mmol) was added thereto at room temperature. The reaction solution was stirred at room temperature for 3 hours more, a saturated aqueous solution of sodium hydrogen carbonate was added and the mixture was extracted with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography (hexane : ethyl acetate = 1:2) to give 530 mg (yield: 74%) of 4-chloro-6-(2-fluoro-1-fluoromethyl-ethoxy)-quinazoline as a yellow solid. The resulting chloro compound (38 mg; 0.147 mmol) and 22 mg (0.147 mmolo) of thiazolo[5,4-b]pyridin-2-yl-amine were heated at 140°C for 2 hours with stirring in 0.2 ml of phenol. Chloroform was added to the reaction solution and the mixture was washed with 1N aqueous solution of sodium hydroxide. The organic layer was dried and concentrated and the resulting residue was purified by a thin layer silica gel chromatography (chlloroform : methanol = 10:1) to give 15 mg (yield: 27%) of the title compound as a yellow solid. 1 HNMR (CDCl3) δ: 4.70-4.73 (2H, m), 4.84-4.86 (2H, m), 4.90-5.02 (2H, m), 7.36 (1H, dd, J = 8.0, 4.4Hz), 7.49 (1H, dd, J = 8.8, 2.8Hz), 7.74 (1H, d, J = 8.8Hz), 7.98 (1H, dd, J = 8.0, 1.6Hz), 8.04 (1H, d, J = 2.8Hz), 8.22 (1H, s), 8.45 (1H, dd, J = 4.4, 1.2Hz) ESI-MS(m/e):374[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-aminothiazolo<5,4-b>pyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: C23H32O7S In N,N-dimethyl-formamide at 20℃; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide | 22 To a stirred solution of 2-aminothiazoio[5,4-b]pyridine {217.4 mg, 1.43 mmol) inDMF {5 mL) was added NaH (60 % in mineral oil, 57.4 mg, 1.43 mmol) at 0 °C.After 30 min, a solution of 109 (217 mg, 0.479 mmol) in DMF (0.5 mL) was added. The reaction mixture was stirred at room temperature overnight and then quenched by 1 N HCl (aq) and acidified. The aqueous solution was extracted with dichloromethane (40 ml_ x 2). The combined organic layer was washed with H2O and brine solution, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (10 % MeOH/ CH2CI2) to give 131 mg of the title compound. MH+ 506 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In sulfolane at 135℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 55℃; for 22h; | 2 To a solution of pyrazole 7 (0.05Og, 0.107mmol) in dichloromethane (5mL) and DMF (I mL) was added amine (0.017g, 0.117mmol), EDC (0.03Og, 0.160mmol), HOBT (0.021 g, 0.160mmol), and triethylamine (0.037mL, 0.267mmol), respectively. Solution heated to 55°C for 22 hours. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel eluting with 0 to 20% of 20% methanol in dichloromethane solution in dichloromethane to afford the product 8 a white solid (8mg, 12%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-aminothiazolo<5,4-b>pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: C24H29N3O4 In tetrahydrofuran; hexane at -78 - 0℃; | 2 To a stirred solution of 16 (240 mg, 0.64 mmol) in anhydrous THF (5 mL) was added 1 ,1'-carbonyldiimidazole (CDI, 125 mg, 0.77 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 hrs. The solution was used in situ for the next step. To a stirred suspension of 2- aminothiazolo[5,4-b]pyridine (388 mg, 2.56 mmol) in anhydrous THF (5 mL) was added dropwise n-BuLi (1.6 M in hexanes, 1.6 mL, 2.56 mmol) at -78 °C and the reaction mixture was stirred at to -78 °C for 1.5 hrs. A solution in THF which is freshly generated above was added slowly into the reaction mixture at -78 °C and the reaction mixture was warmed to 0 °C for 2 hrs. The reaction mixture was acidified with 1 N HCl. The aqueous layer was extracted with dichloromethane (50 mL x 2) and the combined organic layer was washed with 1 N HCl, NaHCO3, H2O and brine solution, dried over MgSO4, filtered and concentrated by rotary evaporator. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1) to give 4-1 (0.167 g,52 %, [M+1] = 507.3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 150℃; for 3h; Microwave irradiation; | 3.11 Example 3-11 2-(2,6-Dichlorophenyl)-1H-indole-6-carboxylic acid thiazolo[5,4-b]pyridin-2-ylamide A mixture of 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (362 mg, 1.18 mmol), thiazolo[5,4-b]pyridin-2-ylamine (179 mg, 1.18 mmol), EDCI (340 mg, 1.77 mmol) and HOBT (176 mg, 1.30 mmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed using a 30-70% gradient of heptane/ethyl acetate to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.95 (s, broad, 1H), 12.00 (s, broad, 1H), 8.51 (dd, J=4.7, 1.4 Hz, 1H), 8.34 (s, 1H), 8.16 (d, J=7.7 Hz, 1H), 7.88 (dd, J=8.5, 1.4 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.3 Hz, 2H), 7.54 (m, 2H), 6.66 (m, 1H). MS (m/z) 439.0 (M+1), Retention time=1.41 min (Method 10). Anal. Calcd.: C, 57.41; H, 2.75; N, 12.75. Found: C, 57.29; H, 2.73; N, 12.54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: 2-aminothiazolo<5,4-b>pyridine With sodium hydride In tetrahydrofuran Stage #2: bis(phenyl) carbonate In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: toluene / 20 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methylate / 1-methyl-pyrrolidin-2-one / 8 h / Reflux 2: sulfuric acid; water / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sulfuric acid; water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: carbon disulfide; 2-aminothiazolo<5,4-b>pyridine With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 0.0833333h; | 3.B Step B: Dimethyl thiazolo[514-b]pyridin-2-ylcarbonimidodithioate; To a suspension of thiazolo[5,4-b]pyridin-2-amine (300 mg, 1.98 mmol) inDMF (2 mL) was added 20.0M sodium hydroxide (200 μ,, 4.0 mmol). The mixture was allowed to stir 10 min at room temperature at which time carbon disulfide was added (300 μ^, 4.96 mmol) and the resulting reddish brown mixture was stirred for 10 minutes. An additional portion of 20 M sodium hydroxide (200 μ, 4.0 mmol) was added and the mixture was again stirred for 10 minutes. Finally, iodomethane (300 μΙ_, 4.76 mmol) was added dropwise. The mixture was stirred for 5 minutes, at which time a voluminous yellow precipitate had formed. The mixture was poured into water and the solids were collected by filtration to afford dimethyl thiazolo[5,4- b]pyridin-2-ylcarbonimidodithioate (190 mg, 38% yield) as a yellow solid of sufficient purity to use without further purification. 1H NM (500 MHz} CDCI3) δ ppm 8.47 (d, J=4.58 Hz, 1 H) 8.1 1 (dd, J-8.24, 1.53 Hz, 1 H) 7.37 (dd, J=8.24, 4.88 Hz, 1 H) 2.66 (s, 6 H). |
38% | Stage #1: 2-aminothiazolo<5,4-b>pyridine With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: carbon disulfide In N,N-dimethyl-formamide for 0.166667h; Stage #3: methyl iodide | 8.A EXAMPLES 8, 8a, 8b; (3R * 4R *)-N-(Thiazolof 5, 4-b]pyridin-2-yl)-4 'H-l-azaspiro[bicyclo[2.2.1 Jheptane-3 5 '-oxazoiJ-2 '-amine; Step A: Dimethyl thiazolo[5,4-b]pyridin-2-ylcarbonimidodithioate; To a suspension of thiazolo[5,4-b]pyridin-2-amine (300 mg, 1.98 mmol) in DMF (2 mL) was added 20.0M sodium hydroxide (200 iL, 4.0 mmol). The mixture was allowed to stir 10 min at room temperature at which time carbon disulfide was added (300 μ,, 4.96 mmol) and the resulting reddish brown mixture was stirred for 10 minutes. An additional portion of 20 M sodium hydroxide (200 iL, 4.0 mmol) was added and the mixture was again stirred for 10 minutes. Finally, iodomethane (300 μ,, 4.76 mmol) was added dropwise. The mixture was stirred for 5 minutes, at which time a voluminous yellow precipitate had formed. The mixture was poured into water and the solids were collected by filtration to afford dimethyl thiazolo[5,4- b]pyridin-2-ylcarbonimidodithioate (190 mg, 38% yield) as a yellow solid of sufficient purity to use without further purification. 1H NMR (500 MHz, CDCk) δ ppm 8.47 (d, J=4.58 Hz, 1 H) 8.11 (dd, J=8.24, 1.53 Hz, 1 H) 7.37 (dd, J=8.24, 4.88 Hz, 1 H) 2.66 (s, 6 H). |
Stage #1: carbon disulfide; 2-aminothiazolo<5,4-b>pyridine With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: methyl iodide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.25h; | 271.A Step A: Dimethyl thiazolo [5,4-b]pyridin-2-ylcarbonimidodithioate To a suspension of thiazolo[5,4-b]pyridin-2-amine(300 mg, 1.98 mmol) in DMF (2 mL) was added 20.0Msodium hydroxide (200 ul., 4.0 mmol). The mixture was allowed to stir 10 min at room temperature at which time carbon disulfide was added (300 ul., 4.96 mmol) and the resulting reddish brown mixture was stirred for 10 minutes. An additional portion of 20.0M sodium hydroxide (200 ul.,4.0 mmol) was added and the mixture was again stirred for 10 minutes. Finally, iodomethane (300 ul., 4.76 mmol) was added dropwise. The mixture was stirred for 5 minutes, atwhich time a voluminous yellow precipitate had formed. Themixture was poured into water and the solids were collectedby filtration to afford dimethyl thiazolo[5,4-b]pyridin-2-ylcarbonimidodithioate(190 mg, 38% yield) as a yellow solid of sufficient purity to use without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water; ethylene glycol / 20 h / 140 °C / Inert atmosphere 2: hydrogenchloride / tetrahydrofuran; water / 5.25 h / 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With hydrogenchloride In water; ethylene glycol at 140℃; for 20h; Inert atmosphere; | 2.3 Step 3: Synthesis of Intermediate E A three-necked reactor equipped with a thermometer was charged with 2.70 g (17.86 mmol) of the intermediate C synthesized in the step 1, 10.38 g (89.29 mmol) of the intermediate D synthesized in the step 2, 1.49 ml (17.86 mmol) of concentrated hydrochloric acid, and 25 ml of ethylene glycol under a nitrogen stream to prepare a homogenous solution. The solution was stirred at 140° C. for 20 hours. After completion of the reaction, the reaction mixture was cooled to 20° C. 300 ml of distilled water and 50 ml of a saturated sodium chloride solution were added to the reaction mixture, followed by extraction with 500 ml of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and sodium sulfate was separated by filtration. The filtrate was concentrated using a rotary evaporator, and the concentrate was purified by silica gel column chromatography (THF:toluene=1:9) to obtain 1.33 g of an intermediate E as a light yellow solid (yield: 30%). The structure of the target product was identified by 1H-NMR. 1H-NMR (500 MHz, DMSO-d6, TMS, δ ppm): 8.07 (dd, 1H, J=1.5 Hz, 5.0 Hz), 7.62 (dd, 1H, J=1.5 Hz, 8.0 Hz), 7.22 (dd, 1H, J=5.0 Hz, 8.0 Hz), 5.46 (s, 2H), 3.70 (t, 2H, J=7.0 Hz), 1.64-1.73 (m, 2H), 1.22-1.35 (m, 6H), 0.86 (t, 3H, J=7.0 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.2% | With hydrogenchloride; hydrazine hydrate In water at 140℃; for 6h; Inert atmosphere; | 1.2 Step 2: Synthesis of Intermediate B Step 2: Synthesis of Intermediate B A four-necked reactor equipped with a thermometer was charged with 1.50 g (9.92 mmol) of the intermediate A synthesized in the step 1, 2.4 ml (49.6 mmol) of hydrazine monohydrate, 0.8 ml (9.92 mmol) of concentrated hydrochloric acid, and 10 ml of ethylene glycol under a nitrogen stream to prepare a homogeneous solution. The solution was stirred at 140° C. for 6 hours. After completion of the reaction, the reaction mixture was cooled to 20° C., followed by addition of 20 ml of water to precipitate a solid, which was filtered off. The solid was washed with water, and dried using a vacuum dryer to obtain 1.47 g of an intermediate B as a yellow solid (yield: 89.2%). The structure of the target product was identified by 1H-NMR. 1H-NMR (400 MHz, DMSO-d6, TMS, δ ppm): 9.30 (brs, 1H), 8.02 (dd, 1H, J=1.4 Hz, 5.0 Hz), 7.54 (dd, 1H, J=1.4 Hz, 8.1 Hz), 7.18 (dd, 1H, J=5.0 Hz, 8.1 Hz), 5.09 (s, 2H) |
76% | With hydrogenchloride; hydrazine hydrate In 1,2-dimethoxyethane; water at 0 - 150℃; for 4h; | 3.2 (2) Synthesis of S16 80% hydrazine hydrate (4.0 mmol) was added to a dry 25 ml eggplant-shaped flask, and the reaction system was placed in an ice water bath and cooled to 0 ° C.Concentrated hydrochloric acid (2.0 mmol) was added dropwise, and reacted at 0 ° C for 10 minutes until no more white smoke was produced.Add 2ml of ethylene glycol and S15 (1.0mmol), heat to 150 ° C for 4h,The reaction was completely converted by TLC, and then cooled to room temperature, and a solid of a large amount of ash was added with water, and filtered, and the cake was dried to obtain S16 (yield 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 1.1.21.1.21.1 1.21.1. tert-butyl 3-(1-((3-(2-azidoethoxy)-5,7-dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)-6-(8-(thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)picolinate [000611] Example 1.2.5 (560 mg) and thiazolo[5,4-b]pyridin-2 -amine (135 mg) were dissolved in dichloromethane (12 mL). N,N-Dimethylpyridin-4-amine (165 mg) and N-ethyl-N'-(3- dimethylaminopropyl)carbodiimide hydrochloride (260 mg) were added, and the reaction stirred at room temperature overnight. The reaction mixture was concentrated, and the crude residue was purified by silica gel chromatography, eluting with 65/35 dichloromethane/ethyl acetate, to provide the title compound. MS (ESI) m/e 829.1 (M+H)+. | |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 1.1.22.1.22.1 1.22.1 tert-butyl 3-(1-((3-(2-azidoethoxy)-5,7-dimethyladamantan-1- yl)methyl)-5-methyl-1H-pyrazol-4-yl)-6-(8-(thiazolo[5,4- b]pyridin-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)- yl)picolinate Example 1.2.5 (560 mg) and thiazolo[5,4-b]pyridin-2-amine (135 mg) were dissolved in dichloromethane (12 mL). N,N-Dimethylpyridin-4-amine (165 mg) and N-ethyl-N’-(3- dimethylaminopropyl)carbodiimide hydrochloride (260 mg) were added, and the reaction stirred at room temperature overnight. The reaction mixture was concentrated, and the crude residue was purified by silica gel chromatography, eluting with 65/35 dichloromethane/ethyl acetate, to provide the title compound. MS (ESI) m/e 829.1 (M+H)+. | |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 1.22.1 1.22.1 tert-butyl 3-(1-( (3-(2-azidoethoxy )-5,7 -dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)-6-(8-( thiazolo[ 5,4-b]pyridin-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)yl)picolinate Example 1.2.5 (560 mg) and thiazolo[5,4-b]pyridin-2-amine (135 mg) were dissolved indichloromethane (12 mL). N,N-Dimethylpyridin-4-amine (165 mg) and N-ethyl-N' -(3-dimethylaminopropyl)carbodiimide hydrochloride (260 mg) were added, and the reaction stirred atroom temperature overnight. The reaction mixture was concentrated, and the crude residue was20 purified by silica gel chromatography, eluting with 65/35 dichloromethane/ethyl acetate, to providethe title compound. MS (ESI) m/e 829.1 (M+Ht |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 1.22.1 1.22.1 tert-butyl 3-(1-((3-(2-azidoethoxy)-5,7-dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)-6-(8-(thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)picolinate Example 1.2.5 (560 mg) and thiazolo[5,4-b]pyridin-2-amine (135 mg) were dissolved in dichloromethane (12 mL). N,N-Dimethylpyridin-4-amine (165 mg) and N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (260 mg) were added, and the reaction stirred at room temperature overnight. The reaction mixture was concentrated, and the crude residue was purified by silica gel chromatography, eluting with 65/35 dichloromethane/ethyl acetate, to provide the title compound. MS (ESI) m/e 829.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-aminothiazolo<5,4-b>pyridine With di(succinimido) carbonate In acetonitrile for 1h; Stage #2: tert-butyl 3-{1-[(3-[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10λ6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(1,2,3,4-tetrahydroquinolin-7-yl)pyridine-2-carboxylate In acetonitrile | 1.53.8 1.53.8 3-{1-[ (3,5-dimethyl-7 -{2-[ (2-sulfoethyl)amino ]ethoxy }tricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H -pyrazol-4-yl }-6-[1-([1,3]thiazolo[ 4,5-b ]pyridin-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl]pyridine-2-carboxylic acid To an ambient suspension of bis(2,5-dioxopyrrolidin-1-yl) carbonate ( 48.2 mg) inacetonitrile (10 mL) was added thiazolo[4,5-b]pyridin-2-amine (34 mg), and the mixture was stirredfor 1 hour. A solution of Example 1.53.6 (220 mg) in acetonitrile (5 mL) was added, and thesuspension was vigorously stirred overnight. The mixture was diluted with ethyl acetate (200 mL),washed with water and brine, and dried over sodium sulfate. Filtration and evaporation of the solvent10 gave a residue, which was dissolved in trifluoroacetic acid (10 mL) and stirred overnight. Afterevaporation of the solvent, the residue was purified by reverse phase HPLC (Gilson system), elutingwith 10-85% acetonitrile in water containing 0.1% v/v trifluoroacetic acid, to provide the titlecompound. 1H NMR (500 MHz, dimethyl sulfoxide-d6) 8 ppm 8.42-8.48 (m, 1H), 8.31-8.40 (m, 4H),8.03 (d, 1H), 7.89 (d, 1H), 7.80 (d, 1H), 7.47 (s, 1H), 7.26-7.37 (m, 2H), 3.93-4.02 (m, 3H), 3.90 (s,15 3H), 3.52-3.60 (m, 3H), 3.17-3.26 (m, 2H), 3.05-3.14 (m, 2H), 2.76-2.89 (m, 5H), 2.23 (s, 3H), 1.90-2.01 (m, 2H), 1.44 (s, 2H), 1.27-1.37 (m, 4H), 0.99-1.22 (m, 5H), 0.88 (s, 6H). MS (ESI) rn/e 855.1(M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-aminothiazolo<5,4-b>pyridine; 7-[6-(tert-butoxycarbonyl)-5-{1-[(3-[13-(tert-butoxycarbonyl)-2,2,7,7-tetramethyl-10,10-dioxido-3,3-diphenyl-4,9-dioxa-10 6-thia-13-aza-3-silapentadecan-15-yl]oxy}-5,7-dimethyltricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}pyridin-2-yl]naphthalene-1-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: With trifluoroacetic acid In dichloromethane | 1.54.3 1.54.3 3-{1-[ (3,5-dimethyl-7 -{2-[ (2-sulfoethyl)amino ]ethoxy }tricyclo[3.3.1.13'7]dec-1-yl)methyl]-5-methyl-1H -pyrazol-4-yl }-6-[8-([1,3]thiazolo[ 4,5-b ]pyridin-2-ylcarbamoyl)naphthalen-2-yl]pyridine-2-carboxylic acid To a solution of Example 1.54.2 (60 mg) in dichloromethane (4 mL) was addedthiazolo[ 4,5-b ]pyridin-2-amine (7 .56 mg), 1-ethyl-3-[3-( dimethylamino )propyl ]-carbodiimidehydrochloride ( 19 mg) and 4-(dimethylamino)pyridine (12.2 mg), and the mixture was stirredovernight. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water and15 brine, and dried over sodium sulfate. Filtration and evaporation of the solvent gave the title product,which was dissolved in dichloromethane/trifluoroacetic acid (1:1, 6 mL) and stirred overnight. Afterevaporation of solvent, the residue was dissolved in N,N-dimethylformamide/water (1:1, 12 mL) andpurified by reverse phase HPLC (Gilson system), eluting with 10-85% acetonitrile in watercontaining 0.1% trifluoroacetic acid, to give the title compound. 1H NMR (400 MHz, dimethyl20 sulfoxide-d6) 8 ppm 13.42 (s, IH), 9.05 (s, IH), 8.51-8.69 (m, 2H), 8.31-8.41 (m, 2H), 8.18-8.26 (m,4H), 8.06 (d, IH), 7.97 (d, IH), 7.68-7.79 (m, IH), 7.49 (s, IH), 7.40 (dd, IH), 3.90 (s, 3H), 3.18-3.29(m, 3H), 3.07-3.15 (m, 2H), 2.82 (t, 3H), 2.24 (s, 3H), 1.44 (s, 2H), 0.97-1.37 (m, IOH), 0.88 (s, 6H).MS (ESI) m/e 850.1 (M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-7-aza-benzotriazole; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 54 LQ076-35: N1-isopropyl-N8-(4-phenylthiazol-2-yl)octanediamide General procedure: A solution of intermediate 11 (35 mg, 0.1 mmol) in DMF, EDCI (24 mg, 0.12 mmol), HOAt (16 mg, 0.12 mmol), isopropylamine (6 mg, 0.1 mmol) and DIEA (19 mg, 0.15 mmol) were added. After the reaction was stirred at RT overnight, the resulting mixture was purified by preparative HPLC (5%-100% acetonitrile / 0.1% TFA in H2O) to afford final compound as white solid (30 mg, 80%). 1H NMR (600 MHz, Methanol-d4) δ 7.90 (d, J = 7.6 Hz, 2H), 7.39 (t, J = 7.6 Hz, 2H), 7.35 (s, 1H), 7.30 (t, J = 7.4 Hz, 1H), 3.99 - 3.93 (m, 1H), 2.49 (t, J = 7.4 Hz, 2H), 2.16 (t, J = 7.5 Hz, 2H), 1.77 - 1.70 (m, 2H), 1.67 - 1.58 (m, 2H), 1.45 - 1.35 (m, 4H), 1.13 (d, J = 6.6 Hz, 6H). MS (ESI): m/z 374.3 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 62 LQ081-176: S-(7-oxo-7-((4-(pyridin-2-yl)thiazol-2-yl)amino)heptyl) 2-methylpropanethioate General procedure: To the solution of intermediate 17 (24 mg, 0.1 mmol) in DMF were treated with 4- (2-pyridinyl)thiazol-2-amine (18 mg, 0.1 mmol), HATU (42 mg, 0.11 mmol) and DIEA (33 μL, 0.2 mmol). After being stirring overnight at room temperature, then the resulting mixture was purified by preparative HPLC (5%-100% acetonitrile / 0.1% TFA in H2O) to afford final compound as white solid (28 mg, 72%). 1H NMR (600 MHz, Methanol-d4) δ 8.77 (d, J = 5.8 Hz, 1H), 8.57 - 8.49 (m, 2H), 8.28 (s, 1H), 7.92 - 7.87 (m, 1H), 2.87 (t, J = 7.3 Hz, 2H), 2.77 - 2.69 (m, 1H), 2.56 (t, J = 7.4 Hz, 2H), 1.75 (p, J = 7.4 Hz, 2H), 1.63 - 1.55 (m, 2H), 1.49 - 1.39 (m, 4H), 1.16 (d, J = 6.9 Hz, 6H). HRMS m/z [M + H]+ calcd for C19H26N3O2S2+ 392.1461, found 392.1467. |
Tags: 31784-70-0 synthesis path| 31784-70-0 SDS| 31784-70-0 COA| 31784-70-0 purity| 31784-70-0 application| 31784-70-0 NMR| 31784-70-0 COA| 31784-70-0 structure
[ 57135-11-2 ]
2-Hydrazinylthiazolo[5,4-b]pyridine
Similarity: 0.88
[ 1160791-13-8 ]
2-Amino-6-bromothiazolo[5,4-b]pyridine
Similarity: 0.84
[ 1355241-53-0 ]
5-Iodothiazolo[5,4-b]pyridin-2-amine
Similarity: 0.84
[ 31784-73-3 ]
2-Aminothiazolo[5,4-b]pyridin-5-ol
Similarity: 0.84
[ 57135-11-2 ]
2-Hydrazinylthiazolo[5,4-b]pyridine
Similarity: 0.88
[ 57135-11-2 ]
2-Hydrazinylthiazolo[5,4-b]pyridine
Similarity: 0.88
[ 1160791-13-8 ]
2-Amino-6-bromothiazolo[5,4-b]pyridine
Similarity: 0.84
[ 1355241-53-0 ]
5-Iodothiazolo[5,4-b]pyridin-2-amine
Similarity: 0.84
[ 31784-73-3 ]
2-Aminothiazolo[5,4-b]pyridin-5-ol
Similarity: 0.84
[ 57135-11-2 ]
2-Hydrazinylthiazolo[5,4-b]pyridine
Similarity: 0.88
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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 |
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