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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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Structure of 103694-26-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 103694-26-4 |
Formula : | C5H8N2S |
M.W : | 128.20 |
SMILES Code : | CC1=NC(=CS1)CN |
MDL No. : | MFCD06212804 |
InChI Key : | ZCKAEFOHSOQKHN-UHFFFAOYSA-N |
Pubchem ID : | 18467479 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 1760 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
330 mg | With hydrazine hydrate; In ethanol; at 20.0℃; for 0.5h; | A mixture of 2-((2-methylthiazol-4-yl)methyl)isoindoline-1 ,3-dione (1 g, 3.87 mmol) and hydrazine hydrate (291 mg, 5.81 mmol, 282 μΙ_) in ethanol (10 mL) was stirred at 20C for 0.5 hour. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol = 0:1 to 10:1 ) to give (2-methylthiazol-4- yl)methanamine (330 mg). |
330 mg | With hydrazine hydrate; In ethanol; at 20.0℃; for 0.5h; | A mixture of 2-((2-methylthiazol-4-yl)methyl)isoindoline-l,3-dione (1 g, 3.87 mmol) and hydrazine hydrate (291 mg, 5.81 mmol, 282 pL) in ethanol (10 mL) was stirred at 20C for 0.5 hour. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol = 0:1 to 10:1) to give (2-methylthiazol-4-yl)methanamine (330 mg). |
330 mg | With hydrazine hydrate; In ethanol; at 20.0℃; for 0.5h; | A mixture of 2-((2-methylthiazol-4-yl)methyl)isoindoline-1,3-dione (1 g, 3.87 mmol) and hydrazine hydrate (291 mg, 5.81 mmol, 282 μL) in ethanol (10 mL) was stirred at 20 C. for 0.5 hour. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol=0:1 to 10:1) to give (2-methylthiazol-4-yl)methanamine (330 mg). |
330 mg | With hydrazine hydrate; In ethanol; at 20.0℃; for 0.5h; | A mixture of 210 2-((2-methylthiazol-4-yl)methyl)isoindoline-1,3-dione (1 g, 3.87 mmol) and 24 hydrazine hydrate (291 mg, 5.81 mmol, 282 μL) in 25 ethanol (10 mL) was stirred at 20 C. for 0.5 hour. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol=0:1 to 10:1) to give 212 (2-methylthiazol-4-yl)methanamine (330 mg). |
330 mg | With hydrazine hydrate; In ethanol; at 20.0℃; for 0.5h; | A mixture of 2-((2-methylthiazol-4-yl)methyl)isoindoline-l,3-dione (1 g, 3.87 mmol) and hydrazine hydrate (291 mg, 5.81 mmol, 282 pL) in ethanol (10 mL) was stirred at 20C for 0.5 hour. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (0902) (dichloromethane:methanol = 0:1 to 10:1) to give (2-methylthiazol-4-yl)methanamine (330 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Add (2-methylthiazol-4-ylmethyl) carbamic acid 2-trimethylsilanyl-ethyl ester (3.5 g, 13.1 mmol) to a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (26.2 mL). Stir at 50C for 2. 5 hours. Concentrate the resulting solution in vacuo to an oil. Dissolve the oil in water, basify with 10% sodium hydroxide and extract with ethyl acetate (2 x 50 mL). Wash the combined organic layers with brine (50 mL), dry (NA2S04), filter and concentrate to an oil. Perform chromatography (silica gel, 93: 7: 1 CHCL3/MEOH/CONCENTRATED NH40H) to afford C-(2-methylthiazol-4-yl)methylamine (140 mg). MS: M/E = 129 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60.0℃; for 18h; | General Procedure: Chloride 8 (0.10 g, 0.35 mmol) was dissolved in DMF (2 mL). Diisopropylethylamine (0.12 mL, 0.70 mmol) and <strong>[103694-26-4](2-methylthiazol-4-yl)methanamine</strong> (0.07 mg, 0.53 mmol) were added and the reaction was stirred at 60 C for 18 h. The crude solution was purified directly by HPLC (Waters 2525 HPLC, Gradient of 20% -> 60% acetonitrile in water) and lyophilized to yield amine 45 as a pure solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With triethylamine; In ethanol; at 20.0℃; for 22h; | General procedure: To a solution of [(1S,2R)-3-[[[3-[(dimethylamino)methylene]-2,3-dihydro-2-oxo-1H- indol-5-yl]sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester 8 (32 mg, 0.050 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 µl, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20 x 20 cm, 500 µm) using 8:2 EtOAc/hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo- 2,3-dihydro- 1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro- furo[2,3-b]furan-3-yl ester 9n (24 mg, 70%). MS m/z 685.3 (MH)+, 1H NMR (CDCl3) 9.15 (m, 1H), 8.70 (s, 1H), 7.66 (s, 1H), 7.61 (d, J = 13.2, 1H),7.43 (dd, J = 8.4, 2.0, 1H), 7.24 (m, 5H), 7.00 (d, J = 8.0, 1H), 5.64 (d, J = 5.2, 1H), 5.11 (d, J = 8.4, 1H), 5.00 (m, 1H), 3.65 - 3.93 (m, 7H), 3.18 (d, J = 6.8, 2H), 2.75 - 3.22 (m, 7H), 1.83 (m, 1H), 1.60 (m, 1H), 1.42 (m, 1H), 1.01 (s, 9H), 0.84 - 0.95 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25.0℃; for 16h; | General procedure: To a solution of 7c (45mg, 0.215mmol) in dry CH2Cl2 (2mL), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCI) (62mg, 0.322mmol), and 1-hydroxybenzotriazole hydrate (HOBt) (50mg, 0.322mmol) were added followed by amine 10a (27mg, 0.215mmol) and diisopropylethylamine (225μL, 1.290mmol). The reaction mixture was stirred at 25C for 16h then CH2Cl2 was added and the resulting solution was washed with saturated aqueous NH4Cl and water. The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/n-hexane 1:4) |
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