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CAS No. : | 894493-95-9 | MDL No. : | MFCD09952017 |
Formula : | C8H18N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FRDZGSBXKJXGNR-YUMQZZPRSA-N |
M.W : | 142.24 | Pubchem ID : | 12188264 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.06 |
TPSA : | 29.26 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.7 cm/s |
Log Po/w (iLOGP) : | 2.12 |
Log Po/w (XLOGP3) : | 0.66 |
Log Po/w (WLOGP) : | 0.82 |
Log Po/w (MLOGP) : | 0.9 |
Log Po/w (SILICOS-IT) : | 0.35 |
Consensus Log Po/w : | 0.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.07 |
Solubility : | 12.1 mg/ml ; 0.0848 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 20.1 mg/ml ; 0.141 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.81 |
Solubility : | 21.9 mg/ml ; 0.154 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
65% | With sodium hydroxide; HClO4; NaH; dimethyl amine In tetrahydrofuran; mineral oil | B. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR62 A solution of trans-2-dimethylamiocyclohexanol (58 g.; 0.405 mole) in 80 ml. of THF was added during 10 minutes to a suspension of NaH (17.05 g.; 0.405 mole of 57percent dispersion in mineral oil) in 240 ml. of THF and the mixture was refluxed for 3 hours. It was cooled to 10°, and methanesulfonyl chloride (46.39 g.; 0.405 mole) was added dropwise during 30 minutes keeping the temperature below 15°. Benzylamine (86.79 g.; 0.81 mole) was then added during 5 minutes, the solvent was evaporated and heating continued at 90° for 16 hours. NaOH (500 ml. of 20percent solution) was added and the mixture heated at 95° for 1 hour, cooled and extracted with ether (5 * 100 ml.). The ether solution was extracted with 10percent HCl (6 * 100 ml.) and backwashed once with ether (discard). The acid extract was cooled, basified with 20percent NaOH and extracted well with ether. The ether solution was washed with H2 O, saturated salt solution, dried (MgSO4) and evaporated. Distillation at 0.4 mm gave 61 g. (65percent yield) of N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine, b.p. 112°. It was identical by tlc to the sample prepared by the reaction of benzylamine with trans-2-chloro-dimethyl-aminocyclohexane. A solution of the benzylamino compound was hydrogenated in two batches each containing 30.5 g. (0.131 mole), 175 ml. EtOH, 3.4 g Pd-C and 56.5 g. (0.394 mole) of 70percent HClO4, at initial pressure of 51.5 p.s.i. for 19 hours. The two batches were combined, filtered through Celite and evaporated in vacuo at 45°. The residue was cooled in ice, basified with 40percent KOH to pH 11. The resulting thick suspension was extracted with ether (5 * 200 ml), the ether extract was dried (MgSO4) and evaporated through a 9 inches Vigreux. The residue was distilled at 13 mm to give 32.5 g. (87percent yield), b.p. 77°-78.5°. Vpc 100percent at 3.8 mm. ir and nmr was identical to those of the sample prepared by the reaction of 7-azabicyclo[3.1.0]heptane with dimethylamine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With chlorosulfonic acid; sodium hydroxide; dimethyl amine In chloroform-d1 | C. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR37 The starting 7-azabicyclo[4.1.0]heptane was best prepared according to the procedure of D. E. Paris and P. E. Fanta, JACS, 74, 3007 (1952) from trans-2-aminocyclohexanol with chlorosulfonic acid, followed by heating with aqueous sodium hydroxide. For the reaction with dimethylamine the procedure described in Bull. Soc. Chim., France, 382 (1956) was followed. A mixture of 7-azabicyclo[4.1.0]heptane (12 g.; 0.124 mole), 40 ml. of aqueous dimethylamine and 0.2 g. of ammonium chloride (NH4 Cl) was stirred and heated on the steam bath for 18 hours and partly evaporated at room temperature in vacuo. Sodium hydroxide (NaOH) was added and the mixture extracted with ether. The extract was dried (MgSO4) and evaporated. Distillation at 16 mm gave 8.1 g. (46percent yield) of the titled compound as a colorless oil. nmr in CDCl3 (100 MHz) was in accord. Mass spectrum (M-8705) M+ 142. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium hydroxide; HClO4; NaH; dimethyl amine;Pd-C; In tetrahydrofuran; mineral oil; | B. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR62 A solution of trans-2-dimethylamiocyclohexanol (58 g.; 0.405 mole) in 80 ml. of THF was added during 10 minutes to a suspension of NaH (17.05 g.; 0.405 mole of 57% dispersion in mineral oil) in 240 ml. of THF and the mixture was refluxed for 3 hours. It was cooled to 10, and methanesulfonyl chloride (46.39 g.; 0.405 mole) was added dropwise during 30 minutes keeping the temperature below 15. Benzylamine (86.79 g.; 0.81 mole) was then added during 5 minutes, the solvent was evaporated and heating continued at 90 for 16 hours. NaOH (500 ml. of 20% solution) was added and the mixture heated at 95 for 1 hour, cooled and extracted with ether (5 * 100 ml.). The ether solution was extracted with 10% HCl (6 * 100 ml.) and backwashed once with ether (discard). The acid extract was cooled, basified with 20% NaOH and extracted well with ether. The ether solution was washed with H2 O, saturated salt solution, dried (MgSO4) and evaporated. Distillation at 0.4 mm gave 61 g. (65% yield) of N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine, b.p. 112. It was identical by tlc to the sample prepared by the reaction of benzylamine with trans-2-chloro-dimethyl-aminocyclohexane. A solution of the benzylamino compound was hydrogenated in two batches each containing 30.5 g. (0.131 mole), 175 ml. EtOH, 3.4 g Pd-C and 56.5 g. (0.394 mole) of 70% HClO4, at initial pressure of 51.5 p.s.i. for 19 hours. The two batches were combined, filtered through Celite and evaporated in vacuo at 45. The residue was cooled in ice, basified with 40% KOH to pH 11. The resulting thick suspension was extracted with ether (5 * 200 ml), the ether extract was dried (MgSO4) and evaporated through a 9 inches Vigreux. The residue was distilled at 13 mm to give 32.5 g. (87% yield), b.p. 77-78.5. Vpc 100% at 3.8 mm. ir and nmr was identical to those of the sample prepared by the reaction of 7-azabicyclo[3.1.0]heptane with dimethylamine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With chlorosulfonic acid; sodium hydroxide; dimethyl amine; In chloroform-d1; | C. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR37 The starting 7-azabicyclo[4.1.0]heptane was best prepared according to the procedure of D. E. Paris and P. E. Fanta, JACS, 74, 3007 (1952) from trans-2-aminocyclohexanol with chlorosulfonic acid, followed by heating with aqueous sodium hydroxide. For the reaction with dimethylamine the procedure described in Bull. Soc. Chim., France, 382 (1956) was followed. A mixture of 7-azabicyclo[4.1.0]heptane (12 g.; 0.124 mole), 40 ml. of aqueous dimethylamine and 0.2 g. of ammonium chloride (NH4 Cl) was stirred and heated on the steam bath for 18 hours and partly evaporated at room temperature in vacuo. Sodium hydroxide (NaOH) was added and the mixture extracted with ether. The extract was dried (MgSO4) and evaporated. Distillation at 16 mm gave 8.1 g. (46% yield) of the titled compound as a colorless oil. nmr in CDCl3 (100 MHz) was in accord. Mass spectrum (M-8705) M+ 142. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Pd on carbon; | D. cis-N,N-dimethyl-1,2-cyclopentanediamine The benzyl carbamate obtained in the previous step C (7.9 g.,) was dissolved in 200 ml. ether, treated with 10% Pd on carbon (2.0 g.) and hydrogenated at Ca. 50 psi for 72 hours. The solution was filtered and the ether removed by distillation. The residue was distilled at reduced pressure to give 1.5 g., (7% overall yield) of the titled diamine, b.p. 90-100/30 mm. ir NH 3300; CH 2940, 2850; N-alkyl 2750; NH def 1590; CH 1460, 1440; CN/other 1350, 1265, 1200, 1140, 1105, 1070, 1040, 900; nmr (CDCl3) was in accord. Mass spectrum M+ 128. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In dichloromethane; at 20℃; | General procedure: Isothiocyanate 4 (0.778 g, 2.0 mmol) was added to a stirred solution of N,N-cyclohexane-1,2-diamine 5a/5b (0.284 g, 2.0 mmol) in dry dichloromethane (25 mL). The reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the crude product was purified using column chromatography eluting with CHCl3/MeOH = 50:1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 12h; | General procedure: A mixture of N-Boc protected 2-isothiocyanato cyclohexylamine [18], [18a] and [18b] (1.0 equiv) and N,N-dimethyl-1,2-substituted diamines [19] and [20] (1.0 equiv) in THF (0.2 M) was stirred for 12 h. The mixture was then concentrated and purified by flash chromatography to afford the thiourea almost quantitatively. The resulting thiourea was dissolved in 4 M HCl-dioxane (3:2, 0.04 M) and stirred overnight to remove the N-Boc group. The pH of the resulting mixture was adjusted to 13-14 by adding 1 M aq NaOH. The mixture was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel to give the desired catalysts 3, 4, 5, 6, and 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.6% | With potassium phosphate; In ethyl acetate; toluene; | To 30 mL of dry toluene add 2-iodo-1-(methoxymethoxy)-4-(2,4,4-trimethylpentan-2-yl)benzene (1.50 g, 3.986 mmol), carbazole (0.633 g, 3.786 mmol), K3PO4 (1.71 g, 8.034 mmol), CuI (0.158 g, 0.830 mmol) and trans-N,N-dimethylcyclohexane-1,2-diamine (0.158 g, 1.111 mmol). Reflux the reaction mixture for 48 hours, cool, filter, and concentrate to give material. Purify material by flash chromatography using 3% ethyl acetate in hexanes to give 0.49 g (29.6%) of 9-(2-(methoxymethoxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl)-9H-carbazole as off-white powder. 1H NMR (400 MHz, CDCl3) delta 8.19-8.14 (m, 2H), 7.50-7.25 (m, 7H), 7.19-7.13 (m, 2H), 4.93 (s, 2H), 3.16 (s, 3H), 1.76 (s, 2H), 1.40 (s, 6H), 0.82 (s, 9H). 13C NMR (101 MHz, CDCl3) delta 151.41 (s), 144.96 (s), 141.46 (s), 127.95 (s), 127.19 (s), 126.13 (s), 125.68 (s), 123.11 (s), 120.13 (s), 119.39 (s), 116.20 (s), 110.05 (s), 94.99 (s), 56.99 (s), 56.06 (s), 38.27 (s), 32.40 (s), 31.85 (s), 31.58 (s); MS m/e 416 (M+Na)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene; at 20℃; for 3h; | (1S,2S)-2-(Dimethylamino)cyclohexylamine (4 [43];1.07 g, 7.5 mmol) was added to a solution of 830 mg2-isothiocyanato-4,6-dimethylpyrimidine (11 [47, 48];5.02 mmol) in 10 cm3 toluene and stirred for 3 h at r.t.The solvent was removed and the residue separated by CC(CH2Cl2/MeOH 30:1-20:1-12.5:1). Evaporation gavecrude 5-1 as foam (1.598 g, quantitative), which retainedsome tBuOMe solvent. 1H NMR (400 MHz, CDCl3):d = 1.10-1.47 (m, 4H), 1.66-1.76 (m, 1H), 1.80-1.94 (m,2H), 2.29 (s, 6H, NMe2), 2.39 (s, 6H, 2 Me), 2.56 (td,J = 10.5, 3.4 Hz, 1H), 2.71-2.76 (m, 1H), 4.15 (ddd,J = 10.5, 6.6, 4.0 Hz, 1H), 6.66 (s, 1H), 8.37 (br s, 1 NH),11.48 (br d, J = 5.7 Hz, 1 NH) ppm; 13C NMR (100 MHz,CDCl3): d = 22.55 (CH2), 23.97 (CH3), 24.77 (CH2),25.24 (CH2), 32.00 (CH2), 40.67 (CH3), 56.81 (CH), 66.77(CH), 114.27 (CH), 157.20 (C), 167.51 br (C), 178.02(C=S) ppm; MS (CI, CH4): m/z = 308.3 (M?H?), 166,124; IR (ATR): v = 3429, 3178, 3030, 2929, 2858, 1598,1511, 1371, 1164, 1040, 788, 706 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene; at 20℃; | (1S,2S)-2-(Dimethylamino)cyclohexylamine (4 [43];594 mg, 4.18 mmol) was added to a solution of 773 mgisothiocyanate 7g (3.48 mmol) in 5 cm3 toluene, and thereaction mixture stirred overnight. Evaporation and purificationby CC (CH2Cl2 and then CH2Cl2/MeOH 30:1-20:1)gave a foam which was crushed to powder, washed withtBuOMe, and dried in vacuum to give colorless solid(1300 mg, quant.), retaining some tBuOMe. A sample foranalysis was further dried in vacuum. 1H NMR (400 MHz,CDCl3): d = 1.07-1.19 (m, 1H), 1.21-1.46 (m, 16H),1.72-1.79 (m, 1H), 1.84-1.96 (m, 2H), 2.25 (s, 6H, NMe2),2.55 (td, J = 10.9, 3.3 Hz, 1H), 2.60-2.67 (m, 1H), 1.98(br s, 2H, iPr-CH), 4.21 (m, 1H), 8.38 (s, 1 NH), 11.11 (d,J = 6.3 Hz, 1 NH) ppm; 13C NMR (100 MHz, CDCl3):d = 20.96 (CH3), 21.00 (CH3), 21.75 (CH2), 24.98 (CH2),25.34 (CH2), 32.33 (CH2), 37.19 br (CH3), 40.37 (CH),57.29 (CH), 66.87 (CH), 162.00 (C), 177.93 (C), 184.67 br(C) ppm; MS (CI, CH4): m/z = 393.4 (M ? C2H5?), 365.3(M ? H?); IR (ATR): v = 3419, 3198, 2931, 2861, 1570br, 1536 br, 1391, 1150, 840 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene; at 20℃; | Isothiocyanate 7a (116 mg, 0.46 mmol) was combinedwith 79 mg (1S,2S)-2-(dimethylamino)cyclohexylamine (4[43]; 0.56 mmol) in 1 cm3 PhMe and stirred overnight.Evaporation and purification by CC (CH2Cl2-CH2Cl2/MeOH 30:1-20:1) gave colorless solid 5-3 (136 mg,75 %). X-ray quality crystals were obtained by slowevaporation from a concentrated toluene solution. 1H NMR(400 MHz, CDCl3): d = 1.08-1.50 (m, 4H), 1.33 (br s,18H, tBu), 1.72-1.99 (m, 3H), 2.24 (br s, 6H, NMe2),2.51-2.62 (m, 2H), 4.23-4.35 (m, 1H), 8.37 (br s, 1 NH),11.07 (br d, J = 6.1 Hz, NH) ppm; 13C NMR (100 MHz,CDCl3): d = 21.68 (CH2), 25.12 (CH2), 25.42 (CH2), 28.84(CH3), 32.69 (CH2), 39.62 (C), 40.36 (CH3), 57.33 (CH),66.89 (CH), 161.85 (C), 178.00 (C), 187.30 br (C) ppm;MS (CI, CH4): m/z = 393.4 (M + H+); IR (ATR): = 3190,3127, 3047, 2935, 2862, 1573, 1510, 1173, 1151,683 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: A solution of the amine (1 equiv) in ethanol (10 mL per gram of amine), was added dropwise to an icecooled solution of 2-[2-(bromomethyl)-phenyl]benzene carbaldehyde 17 (1.1 equiv) in ethanol (10 mL pergram of 17). The reaction mixture was stirred overnight while attaining ambient temperature. Sodium tetraphenylborate (1.1 equiv) in the minimum amount of acetonitrile was added in one portion to thereaction mixture and after 5 minutes of stirring, the organic solvents were removed under reduced pressure.Ethanol was added to the residue, followed by few drops of water. The resulting solid was collected byfiltration and washed with additional ethanol followed by diethyl ether. If no solid materialises after theaddition of the water the suspension is allowed to settle and the ethanol/water phase is decanted off. Thegummy residue was macerated in hot ethanol or methanol. The organic salt may then precipitate but in somerare cases it does so upon slow cooling of the hot alcoholic solution. If solubility problems do arise, smallamounts of acetonitrile may be added during this process. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 4h; | HATU (4268 mg, 11.22 mmol) was added to a mixture of 2-(4-bromo-2-chlorophenoxy)acetic acid (2655 mg, 10.00 mmol), (1 S,25)-N?,N?-dimethylcyclohexane-l, 2-diamine (1494 mg, 10.50 mmol) and triethylamine (3.50 mE, 25.1 mmol) in 30 ml of DMF. The mixture was stirred for 4 hours, concentrated in vacuum and the residue partitioned between water and ethyl acetate. The organic extracts were washed with sat. NaHCO3, water, brine, dried over Na2504 and concentrated to give 2-(4-bromo-2-chlorophe- noxy)-N-((1 S,25)-2-(dimethylamino)cyclohexyl)acetamide (4010 mg, 100%) as a colorless oil, which was used without further purification in the next step. ECMS (ESI) m/z: 389.1 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; | To a solution of N-(2,4-dimethoxybenzyl)-2,4-dif- luoro-N-(thiazol-2-yl)-5-(trifluoromethyl)benzenesulfona-mide (100 mg, 0.20 mmol) and N,N-diisopropylethylamine (0.17 mE, 1.01 mmol) in DMF (5 mE) was added (1 5,25)- N?,N?-dimethylcyclohexane-1,2-diamine (58 mg, 0.40 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with EtOAc (30 mE), washed with water (20 mE), brine (20 mE), dried over anhydrous Na2504, filtered and concentrated in vacuo to give the title compound (100 mg, crude) as a light yellow solid that required no thrther purification. ECMS (ESI) mlz:617.3 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 20℃; for 16h; | To a solution of 5-chloro-N-(2,4-dimethoxyben- zyl)-2,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide (1.04 g, 2.25 mmol) and K2C03 (0.93 g, 6.75 mmol) in DMF (25 mE) was added (1 S,25)-N?,N?-dimethylcyclohexane-l ,2- diamine (0.32 g, 2.25 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with EtOAc (100 mE), washed with water (100 mEx3), brine (100 mE), dried over anhydrous Na2504, filtered and concentrated in vacuo to give the title compound (1.2 g, crude) as a brown solid that required no thrther purification. ECMS (ESI) mlz: 583.1 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; | To a solution of 5-bromo-N-[(2,4-dimethoxyphe-nyl)methyl] -2,4-difluoro-N-thiazol-2-yl-benzenesulfona-mide (300 mg, 0.59 mmol) in DMF (3 mE) was addedpotassium carbonate (246 mg, 1.78 mmol) and (15,25)-N?,N?-dimethylcyclohexane-1,2-diamine (93 mg, 0.65mmol). The reaction mixture was stirred at room temperature for 16 h. Water (10 mE) was added and extracted withEtOAc (10 mEx2). The combined organic layers werewashed with water (10 mEx3), brine (15 mE), dried overanhydrous Na2504, filtered and concentrated in vacuo togive the title compound (187 mg, crude) as a yellow solidthat required no further purification. ECMS (ESI) mlz: 627[M+H]. |
Tags: 894493-95-9 synthesis path| 894493-95-9 SDS| 894493-95-9 COA| 894493-95-9 purity| 894493-95-9 application| 894493-95-9 NMR| 894493-95-9 COA| 894493-95-9 structure
A1471251[ 320778-92-5 ]
(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine
Reason:
A226184[ 320778-92-5 ]
(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine
Reason: Optical isomers
[ 61798-24-1 ]
N1,N2-Dimethylcyclohexane-1,2-diamine
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