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CAS No. : | 181258-46-8 | MDL No. : | MFCD03425263 |
Formula : | C10H18BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OSMADJAEHVCZKN-UHFFFAOYSA-N |
M.W : | 264.16 | Pubchem ID : | 14821711 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 1760 |
Hazard Statements: | H302-H314 | 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 |
---|---|---|
20% | To a solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 50 mg, 0.2 mmol) in N,N-dimethylformamide (0.5 mL) was added powdered sodium hydroxide (12 mg, 0.31 mmol) and tetrabutylammonium hydrogen sulfate (3 mg, 0.009 mmol). The mixture was stirred at room temperature for 30 min then <strong>[181258-46-8]tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate</strong> (67 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 4 days. Water (5 ml) was added to the mixture, followed by HCl (3% aqueous, 1 mL). The mixture was extracted with ethyl acetate (3*30 ml). The extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (12 g silica, methylene chloride to 90/10 methylene chloride/methanol gradient) to yield tert-butyl 2-[2-amino-3-(aminocarbonyl)-9H-pyrido[2,3-b]indol-9-yl]methyl}pyrrolidine-1-carboxylate (xvi-e, 20 mg, 20%). NH4OAc QC conditions. M+1=410. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 90℃; for 1.5h;Neat (no solvent); | Example 35; 10-(alpha-Benzylpyrrolidin-2-vnmethvn-7.8-dimethylbenzofglpteridine-2.4(3H.10H)- dione; Scheme 7; Step 1 Preparation of tert-butyl 2-(((2-amino-4,5- dimethylphenvDamino^methvDpyrrolidine-1-earboxylate; [0145] tert-Butyl 2-(((2-amino-4,5-dimethylphenyl)amino)methyl)pyrrolidine- 1 - carboxylate is synthesized by preparing a neat mixture of tert-butyl 2- (bromomethyl)pyrrolidine-1-carboxylate (475 mg, 1.8 mmol) and 4,5-dimethylbenzene- 1,2-diamine (272 mg, 2.0 mmol), and heating the resulting paste to 90 C for 1.5 h. The resulting liquid is cooled to room temperature and taken onto the next step without further purification. LC-MS m/z 319.9 [M+H], retention time 3.57 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 80 - 90℃; for 8h; | rac-A -(1 -(Pyrrolidin-2-ylmethyl)-1 H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide Step 1 : To /V-(1 H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (150 mg, 0.56 mmol) in DMF (1 .5 mL), ferf-butyl 2-(bromomethyl)pyrrolidine-1 -carboxylate (148 mg, 0.56 mmol) was added and K2C03 (309 mg, 2.24 mmol) followed by tetrabutylammoniumbromide (18 mg, 0.056 mmol). The reaction mixture was heated to 80 C for 2 h, then ferf-butyl 2- (bromomethyl)pyrrolidine-l-carboxylate (1 eq.) followed by heating to 90 C for 6 h. The reaction mixture was diluted with EtOAc, washed with sat. aq. NaHC03-solution (1x) and brine (1x). The aq. layers were reextracted with EtOAc (1 x). The combined organic layers were dried (MgS04), filtered and the solvent was removed under reduced pressure. Purification by FC (EtOAc/ hex 9:1 , Rf= 0.45) yielded rac-ferf-butyl 2-((4-(5-(m-tolyl)oxazole- 4-carboxamido)-1 /-/-pyrazol-1 -yl)methyl)pyrrolidine-1 -carboxylate as a yellow foam. LC-MS conditions A: tR = 0.94 min, [M+H]+= 452.23. |
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