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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.
Tranylcypromine is a dual inhibitor of both MAO-A/B and LSD1.
Synonyms: SKF 385 hydrochloride; Tranylcypromine (hydrochloride); trans-2-Phenylcyclopropylamine
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 1986-47-6 |
Formula : | C9H12ClN |
M.W : | 169.65 |
SMILES Code : | N[C@H]1[C@H](C2=CC=CC=C2)C1.[H]Cl |
Synonyms : |
SKF 385 hydrochloride; Tranylcypromine (hydrochloride); trans-2-Phenylcyclopropylamine
|
MDL No. : | MFCD00063602 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 |
Class: | 6.1 |
UN#: | 2811 |
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 |
---|---|---|
With O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 24.5h; | 304 mg (0.928 mmol, 1.05 equivalents) of TOTU and 323 mul (1.857 mmol, 2.1 equivalents) of ethyldiisopropylamine were added to 0.973 mmol (1.0 equivalent) of the respective carboxylic acid in 2 ml of absolute dimethylformamide at 0C and the mixture was stirred for 20 minutes at 0C. Subsequently, 0.884 mmol (1.0 equivalent) of the respective arylcycloalkylamine hydrochloride, dissolved in 2 ml of absolute dimethylformamide, were added and the mixture was stirred for 30 minutes at 0C and for 24 h at room temperature. The reaction mixture was filtered, the filter cake washed with 20 ml of ethyl acetate and the resulting solution washed with 20 ml of 5% aqueous sodium hydrogencarbonate solution and 20 ml of 5% aqueous sodium chloride solution. The organic phase was dried over Chromabond XTR and evaporated. The obtained raw product was purified by preparative HPLC (RP-18, acetonitrile/water + 0.1 % trifluoroacetic acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. | |
Example 7: frans-(+/-)-Benzyl-(2-phenyl-cyclopropyl)-amine 11; [000204] To a stirred solution of trans-(+/-)-2-Phenylcyclopropylamine hydrochloride (50 mg, 0.295 mmol) in MeOH (1 ml_) were added benzaldehyde (27 uL, 0.266 mmol) and sodium cyanoborohydride (22 mg, 0.354 mmol). The mixture was stirred at 0 C for 1 h followed at room temperature overnight. To the reaction mixture was added crushed ice, and the acetonitril was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (15.4 mg). 1H NMR (CDCI3): delta (ppm) 7.40-7.25 (m, 9 H), 7.18 (m, 1 H), 7.03 (d, 2 H, J = 7.3 Hz), 3.92 (s, 2 H), 2.42 (m, 1 H), 2.25 (m, br. s, 1 H), 1.97 (m, 1 H), 1.14 (m, 1 H), 1.01 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.7, 140.7, 128.8 (2), 128.7 (2), 128.6 (2), 127.4, 126.3 (2), 125.9, 54.0, 41.6, 25.8, 17.5. HRMS (ESI) calculated for Ci6Hi8N+ [MH+] 224.1439; found, 224.1440. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In tetrahydrofuran; at -15 - 20℃; for 1.5h; | Example 3: Preparation of trans-(+/-)-Methyl-(2-phenyl-cyclopropyl)-amine; 7[000199] Acetic formic anhydride was generated by dropwise addition of formic acid (0.36 mL, 9.6 mmol) to acetic anhydride ( 0.73 ml_, 7.8 mmol) maintained on ice followed at 50 C for 2 h. The mixture was cooled to room temperature, and THF (5 mL) was added. This mixture (0.6 mL) containing acetic formic anhydride (0.3 mmol) was added to a solution of trans-(+/-)-2-phenyl-cyclopropylamine hydrochloride (50 mg, 0.3 mmol) in THF (1 mL) at -15 C followed by addition of Lambda/-methylmorpholine (45 uL, 0.3 mmol). The resulting mixture was stirred at -15 C for 30 min and at room temperature for 1 h, filtered out insoluble materials, and concentrated in vacuo. The crude residue (65 mg) was dissolved in THF (1.2 mL), and to the solution was added 1.0 M solution of borane dimethylsulfide complex in THF (0.75 mL). After the mixture was stirred at 65 C overnight, the reaction was quenched by 10% aqueous HCI. The mixture was concentrated under reduced pressure to remove THF, and the residual aqueous solution was washed with Et2theta (x1), neutralized with 10% aqueous NaOH, and then extracted with Et2O (x3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N/MeOH (8:1:1) as a developing solvent to afford the title compound as a colorless oil (21 mg). 1H NMR (CDCI3): delta (ppm) 7.30-7.25 (m, 2 H), 7.20-7.16 (m, 1 H), 7.09-7.06 (m, 2 H), 2.54 (br. s, 3 H), 2.34 (m, 1 H), 1.92 (m, 1 H), 1.76 (br. s, 1 H), 1.12-1.06 (m, 1 H), 1.02-0.98 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.8, 128.6 (2), 126.3 (2), 125.9, 43.7, 36.2, 25.3, 17.5. HRMS (ESI) calculated for C10Hi4N+ [MH+] 148.1126; found, 148.1124. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In tetrahydrofuran; at -15 - 20℃; for 1.5h; | Example 4: fra/7s-(+/-)-Methyl-(2-phenyl-cyclopropylmethyl)-amine; 8[000200] Acetic formic anhydride was generated by dropwise addition of formic acid (0.18 mL, 4.8 mmol) to acetic anhydride ( 0.365 ml_, 3.9 mmol) maintained on ice followed at 50 C for 2 h. The mixture was cooled to room temperature, and THF (4.5 mL) was added. This mixture (0.53 mL) containing acetic formic anhydride (0.408 mmol) was added to a solution of trans-(+/-)-2-phenyl-cyclopropylmethylamine hydrochloride (30 mg, 0.163 mmol) in THF (1 mL) at -15 C followed by addition of Lambda/-methylmorpholine (17.9 uL, 0.163 mmol). The resulting mixture was stirred at -15 "C for 30 min and at room temperature for 1 h, filtered out insoluble materials, and concentrated in vacuo.[000201] The crude residue (42 mg) was dissolved in THF (1.2 mL), and to the solution was added 1.0 M solution of borane dimethylsulfide complex in THF (0.41 mL). After the mixture was stirred at 65 C overnight, the reaction was quenched by 10% aqueous HCI. The mixture was concentrated under reduced pressure to remove THF, and the residual aqueous solution was washed with Et2O (x1), neutralized with 10% aqueous NaOH, and then extracted with Et2O (x3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et.3N/MeOH (8:1:1) as a developing solvent to afford the title compound as a colorless oil (14.0 mg). 1H NMR (CDCI3):delta (ppm) 7.29-7.24 (m, 2 H), 7.18-7.15 (m, 1 H), 7.10-7.07 (m, 2 H), 2.66 (br. d, 2 H), 2.49 (br. s, 3 H), 2.37 (br. s, 1 H), 1.77 (m, 1 H), 1.38-1.32 (m, 1 H), 0.99-0.85 (m, 2 H). 13C NMR (CDCI3): delta (ppm) 143.3, 128.7, 126.2, 125.9, 56.5, 36.5, 23.3, 22.5, 15.1. HRMS (ESI) calculated for CnH16N+ [MH+] 162.1283; found, 162.1285. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; sodium cyanoborohydride; acetic acid; In water; acetonitrile; at 20℃; for 0.666667h; | Example 5: frans-(+/-)-Dimethyl-(2-phenyl-cyclopropyl)-amine; 9[000202] To a stirred solution of fra/7s-(+/-)-2-Phenylcyclopropylamine hydrochloride (34 mg, 0.2 mmol) in acetonitrile/H2theta (1 :1 , v/v) (5 ml_) were added N- methylmorpholine (45 uL, 0.4 mmol), 37% aqueous formaldehyde (0.16 mL, 2.0 mmol), and sodium cyanoborohydride (40 mg, 0.6 mmol). Glacial acetic acid (40 uL) was added to the mixture over 10 min and the reaction was stirred at room temperature for 30 min. To the reaction mixture was added crushed ice, and the acetonitrile was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (19.7 mg). 1H NMR (CDCI3): delta (ppm) 7.34-7.26 (m, 2 H), 7.18 (t, 1 H, J = 7.3 Hz), 7.09 (d, 2 H, J = 7.2 Hz), 2.74 (d, 2 H, J = 3.6 Hz), 2.42 (s, 6 H), 2.00 (m, 1 H), 1.83 (m, 1 H), 1.13 (m, 1 H), 0.99 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.5, 128.6 (2), 126.5 (2), 126.0, 50.6, 45.4 (2), 25.7, 17.6. HRMS (ESI) calculated for CnH16N+ [MH+] 162.1283; found, 162.1279. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 6: Preparation of trans-(+/-)-lsopropyl-(2-phenyl-cyclopropyl)-amine 10; [000203] To a stirred solution of trans-(+/-)-2-Phenylcyclopropylamine hydrochloride (50 mg, 0.295 mmol) in MeOH (1 mL) were added acetone (21.7 uL, 0.295 mmol) and sodium cyanoborohydride (22 mg, 0.354 mmol). The mixture was stirred at 0 C for 1 h followed at room temperature overnight. To the reaction mixture was added EPO <DP n="79"/>crushed ice, and the acetonitril was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (16.7 mg). 1H NMR (CDCI3): delta (ppm) 7.30-7.25 (m, 2 H), 7.19-7.14 (m, 1 H), 7.06 (d, 2 H, J = 7.3 Hz), 3.01 (m, 1 H), 2.31 (m, 1 H), 1.90 (m, 1 H), 1.87 (br. s, 1 H), 1.12 (d, 6 H, J = 6.3 Hz), 1.07 (m, 2 H). 13C NMR (CDCI3): delta (ppm) 142.8, 128.6 (2), 126.1 (2), 125.8, 49.7, 40.7, 25.9, 23.7, 23.6, 17.2. HRMS (ESI) calculated for Ci2H18N+ [MH+] 176.1439; found, 176.1437. |