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CAS No. : | 186550-13-0 | MDL No. : | MFCD01861220 |
Formula : | C9H18N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CMIBWIAICVBURI-UHFFFAOYSA-N |
M.W : | 186.25 | Pubchem ID : | 2756370 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P264-P270-P280-P301+P310-P305+P351+P338-P310-P321-P330-P405-P501 | UN#: | 2810 |
Hazard Statements: | H301-H318 | 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 |
---|---|---|
(+-)-N-[7-(1-Butyryl-pyrrolidin-3-ylsulfamoyl)-indan-4-yl]-2-methyl-benzamide (H-71) The title compound was made following general procedure in Scheme 10, substituting <strong>[32202-61-2]indan-4-ylamine</strong> for 5,6,7,8-tetrahydro-naphthalen-1-yl amine and 3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester for 4-amino-piperidine-1-carboxylic acid tert-butyl ester 1H NMR (300 MHz, CDCl3) delta 8.22 (m, 1H), 7.76 (dd, 1H), 7.49 (m, 2H), 7.39 (m, 1H), 7.28 (m, 2H), 5.32 (dd, 1H), 3.80 (m, 1H), 3.40 (m, 5H), 2.88 (t, 2H); 2.52 (s, 3H), 2.20 (m, 6H), 1.90 (m, H), 1.60 (m, 2H), 0.84 (t, 3H); LC/MS m/z 470 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1: (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine; hydrochloride A mixture of 470 mg (2.5 mmol) <strong>[3621-82-7]2,6-dichloro-benzooxazole</strong> (commercially available), 511 mg (2.75 mmol) 3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (commercially available) and 328 mg (3.25 mmol) NEt3 in 8 mL DCM was stirred at room temperature over night. KHSO4 aq (1N) was added and the organic layer was evaporated under reduced pressure. The residue was taken up in 10 mL HCl in dioxane (4N) and concentrated under reduced pressure to yield the crude title compound which was used without further purification in the consecutive step. (MH+) 238.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 16h;Inert atmosphere; Cooling with ice; | General procedure: 4-Fluoro-2-(trifluoromethyl)benzoic acid (1 equiv), amine (1 equiv) and DMAP (0.1 equiv) were added to THF (50mL) under nitrogen. The obtained solution was cooled down on an ice-water bath. EDC·HCl (1.3 equiv) was added to the solution, and the reaction mixture was stirred for 16h while warming at room temperature. The reaction solution was washed with water and extracted with EtOAc, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to yield pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In 1-methyl-pyrrolidin-2-one; at 180℃; for 1h;Microwave irradiation; | A mixture of 14 <strong>[84946-20-3]2-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole</strong> (2) (261mg, 1mmol) and 133 tert-butyl 3-aminopyrrolidine-1-carboxylate (370μL, 2mmol) in NMP (2mL) was heated at 180C under microwave for 60min. After cooling down to room temperature, the mixture was treated with a saturated 134 NaHCO3 solution and extracted with EtOAc. The combined organic phases was washed with water (2 times), dried over Na2SO4, and evaporated in vacuo. The crude residue was purified by silica gel flash column chromatography to afford the 135 title compound 18 (168mg, 54%). 1H NMR (300MHz, CDCl3) δ=7.53 (d, J=7.8Hz, 1H), 7.18-7.05 (m, 3H), 7.05-6.91 (m, 4H), 5.20 (s, 2H), 3.77-3.60 (m, 3H), 3.54 (ddd, J=9.7, 7.9, 6.2Hz, 1H), 3.26 (dd, J=9.4, 4.1Hz, 1H), 2.25 (br s, 2H), 2.18-2.06 (m, 1H), 1.79-1.65 (m, 1H)ppm. 13C NMR (75MHz, CDCl3) δ=162.11 (d, J=246.1Hz), 156.76, 142.16, 135.93, 132.52 (d, J=3.1Hz), 127.43 (d, J=8.0Hz), 121.98, 120.25, 116.76, 115.87 (d, J=21.6Hz), 108.28, 58.73, 51.21, 48.95, 47.08, 34.70ppm. HRMS m/z [M+H]+ calcd for C18H20FN4: 311.1666, found: 311.1662. |
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