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CAS No. : | 6530-09-2 | MDL No. : | MFCD00137395 |
Formula : | C7H16Cl2N2 | Boiling Point : | - |
Linear Structure Formula : | C7H12N(NH2)·2HCl | InChI Key : | STZHBULOYDCZET-UHFFFAOYSA-N |
M.W : | 199.12 | Pubchem ID : | 197853 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 2.5h; | Acid C9 (1.96 g, 12.0 MMOL), DIEA (6.27 mL, 36.0 mmol), and R- (+)-3- aminoquinuclidine dihydrochloride (2. 42 g, 12.1 mmol) are added to DMF (60 mL), and the reaction is cooled in an ice bath. HATU (4.57 g, 12.0 mmol) is added, the solution allowed to warm to rt over 2.5 h, then CONCENTRATED IN VACUO. The residue is stirred with saturated NAHCO3 (30 mL) for 30 min, then extracted with CHC13 (10 X 50 mL). The combined organic layer is dried (NA2S04) and is concentrated in vacuo. The crude material is chromatographed over 130 g slurry-packed silica gel, eluting with 0.5% ammonium hydroxide in 10% MEOH/CHC13. The appropriate fractions are combined and concentrated to a residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
529 mg of <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong> hydrate are dissolved in 18 mi of DMF, followed by addition of 508 mg of 1-hydroxy-benzotriazol and 1.81 G of dicyclohexyl-carbodiimide. After stirring for 1 h at r. t. , the precipitated dicylohexyl-urea is filtered off and 500 mg of 3 (S)- aminoquinuclidine dihydrochloride and 1.3 ml of ethyl-diisopropylamine is added to the filtrate. After stirring for 48 h at room temperature, a second portion of dicylohexyl-urea is filtered off and washed with MeOtBu/DMF (4: 1). Wash solution and filtrate are combined and crystallized by standing over night at 5° The crystalline precipitate is filtered off and washed with MeOtBu/DMF (4: 1), followed by MeOtBu to yield the title compound as monohydrochloride. NMR (1H, 400 MHz, AH d6-DMSO) : 1.75 (1H, t), 1.96 (2H, m), 2.12 (1H, q), 2.24 (1H, d), 3.24 (3H, m), 3.43 (2H, m), 3.65 (1'H, t), 4.49 (1H, q), 7. 86 (1H, t), 7.92 (1H, t), 8. 24 (1H, d), 8.30 (1H, d), 8. 61 (1H, s), 9.31 (1 H, d), 9. 46 (1H, s), 10.59 1H, br). MS (ES+) : 282 (MH)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20℃; for 24h; | General procedure: Method 3: [0050] After 300 mg (1.39 mmol) of <strong>[77837-08-2]6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid</strong> was dissolved in 10 mL of acetonitrile, 415 mg (2.08 mmol) of 3-aminoquinuclidine dihydrochloride and 718 mg (5.56 mmol) of diethylisopropylamide were added to the solution. Afterward, 207 mg (1.53 mmol) of 1-hydroxylbenzotriazole (HOBt) and 266 mg (1.39 mmol) of N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDC) were added to the reaction solution. This reaction solution was stirred at room temperature for about 24 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo and then extracted three times with chloroform and an aqueous NaOH solution (pH=12), followed by purification using liquid chromatography (chloroform:methanol: ammonia water=10:1:0.1) to obtain a target compound (Actual yield: 317 mg, Percent yield: 70percent). [0051] 1H-NMR (CDCl3,200 MHz) delta8.11 (s, 1H), 7.75 (d, 1H), 7.40 (m, 4H), 6.65 (d, 1H), 6.26 (br, 1H), 4.15 (m, 1H), 3.39 (m, 1H), 2.89 (m, 4H), 2.53 (m, 1H), 2.06 (m, 1H), 1.53 (m, 4H) |
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