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[ CAS No. 14683-47-7 ] {[proInfo.proName]}

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Product Details of [ 14683-47-7 ]

CAS No. :14683-47-7 MDL No. :MFCD00467853
Formula : C14H15N Boiling Point : -
Linear Structure Formula :CH3NHCH(C6H5)2 InChI Key :SHDMMLFAFLZUEV-UHFFFAOYSA-N
M.W : 197.28 Pubchem ID :411467
Synonyms :

Calculated chemistry of [ 14683-47-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.5
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 2.67
Log Po/w (MLOGP) : 3.34
Log Po/w (SILICOS-IT) : 3.28
Consensus Log Po/w : 2.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.3
Solubility : 0.0996 mg/ml ; 0.000505 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.289 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.41
Solubility : 0.000776 mg/ml ; 0.00000394 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 14683-47-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14683-47-7 ]

* 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.

  • Downstream synthetic route of [ 14683-47-7 ]

[ 14683-47-7 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 14683-47-7 ]
  • [ 2567-29-5 ]
  • benzhydryl-methyl-(4-phenyl-benzyl)-amine [ No CAS ]
  • 2
  • [ 119-61-9 ]
  • [ 74-89-5 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: benzophenone; methylamine With titanium(IV) isopropylate In methanol at 20℃; for 5h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2h;
55% With sodium tetrahydroborate; acetic acid at 20℃; for 1.5h;
With ethanol Behandeln des Reaktionsprodukts mit Aethanol und Natrium;
With formic acid at 200℃;

  • 3
  • [ 19836-78-3 ]
  • [ 14683-47-7 ]
  • [ 88563-98-8 ]
YieldReaction ConditionsOperation in experiment
60% With lithium In diethyl ether at -20℃; for 0.166667h;
  • 4
  • [ 13280-16-5 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
95% With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-Methyldicyclohexylamine; water In acetonitrile at 15 - 20℃; Inert atmosphere; Sealed tube; Irradiation;
85% With sodium tetrahydroborate In isopropyl alcohol at 60 - 70℃; for 3h;
69% With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 20 - 60℃;
60% With lithium aluminium tetrahydride In tetrahydrofuran
In isopropyl alcohol Irradiation;
With sodium tetrahydroborate
With sodium hydrogen telluride In ethanol for 0.5h; Ambient temperature; Yield given;
With potassium <i>tert</i>-butylate; hydrogen In benzene for 24h;
With potassium <i>tert</i>-butylate; hydrogen In benzene for 24h;
With potassium <i>tert</i>-butylate; hydrogen In benzene for 24h;
With potassium <i>tert</i>-butylate; hydrogen In benzene for 24h;

  • 5
  • [ 14683-47-7 ]
  • [ 104619-32-1 ]
  • [ 104619-44-5 ]
YieldReaction ConditionsOperation in experiment
With lithium In diethyl ether at -20℃; for 0.166667h;
  • 6
  • [ 14683-47-7 ]
  • [ 94193-37-0 ]
  • [ 94193-43-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In tetrahydrofuran for 1h; Ambient temperature; Yield given;
  • 7
  • [ 614-30-2 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
66% With n-butyllithium; potassium <i>tert</i>-butylate In hexane for 48h; Heating;
  • 8
  • [ 14683-47-7 ]
  • [ 99814-64-9 ]
  • [ 171669-60-6 ]
YieldReaction ConditionsOperation in experiment
82% In water; acetonitrile Ambient temperature;
In water; acetonitrile Ambient temperature;
  • 9
  • [ 14683-47-7 ]
  • [ 99814-64-9 ]
  • [ 171669-60-6 ]
  • 4-(Benzhydryl-methyl-amino)-5-(4-methoxy-phenoxy)-[1,2]benzoquinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In water; acetonitrile Ambient temperature;
  • 10
  • [ 14683-47-7 ]
  • [ 541-41-3 ]
  • ethyl N-benzhydryl-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In dichloromethane for 96h; Ambient temperature;
  • 11
  • [ 14683-47-7 ]
  • [ 873-51-8 ]
  • C6H5CH(C6H5)N(CH3)B(Cl)(C6H5) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane at 0℃; for 1h;
With triethylamine In hexane 0°C, 1 h; Et3N added; 20°C, 1 h; NMR;
  • 12
  • [ 27865-53-8 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
100% With indium; ammonium chloride In ethanol for 4h; Heating;
98% With indium; ammonium chloride; zinc In ethanol; water for 10h; Reflux; chemoselective reaction;
  • 13
  • [ 14683-47-7 ]
  • [ 56613-60-6 ]
  • [ 1009369-71-4 ]
YieldReaction ConditionsOperation in experiment
46% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h; 1.1 A solution of 2.0 mmol N-(diphenylmethyl)methylamine, 2.0 mmol (3-phenyl- propionylamino) -acetic acid (CA [56613-60-6]) and 6.0 mmol DIPEA in 10 ml of acetonitrile was treated with 2.2 mmol of TBTU. After 2 hours at room temperature, the reaction mixture was concentrated, diluted with water and extracted 3 times with ethyl acetate. The organic phase was dried and the residue purified by chromatography (SiC^; dichloromethane / methanol) to give the title compound as a slightly yellowish solid. Yield = 46%. MS (m/e): 385.2 (MH", 100%).
  • 14
  • 1-benzhydryl-1,3-dimethylurea [ No CAS ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
84% With diisobutylaluminium hydride In toluene for 48h; Heating;
  • 15
  • [ 213134-27-1 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 2: 84 percent / DIBAL / toluene / 48 h / Heating
  • 16
  • C-phenyl-N-methylnitrone [ No CAS ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: 100 percent / In; sat. aq. NH4Cl / ethanol / 4 h / Heating
  • 17
  • phenylmagnesium bromide [ No CAS ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: 100 percent / In; sat. aq. NH4Cl / ethanol / 4 h / Heating
  • 18
  • [ 14683-47-7 ]
  • 2-methyl-1,3-diphenyl-2,3-dihydro-1<i>H</i>-benzo[<i>c</i>][1,2]azaborole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hexane / 1 h / 0 °C 2: Al2Cl6 / CH2Cl2 / 0.5 h / 0 °C
  • 19
  • [ 14683-47-7 ]
  • 1-benzyl-4-piperidyl N-benzhydryl-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / Et3N / CH2Cl2 / 96 h / Ambient temperature 2: 1.) CH3ONa / 1.) MeOH, 2.) toluene, reflux, 1 d
  • 20
  • [ 14683-47-7 ]
  • {2-Amino-5-[3-(benzhydryl-methyl-carbamoyl)-propoxy]-benzylamino}-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. Na2CO3 / tetrahydrofuran / 1 h / Ambient temperature 2: 1.) AcONa / ethanol / 0.5 h 3: NaBH3CN / ethanol / 3 h 4: H2 / 10percent Pd/C / ethanol
  • 21
  • [ 14683-47-7 ]
  • [ 94192-78-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: aq. Na2CO3 / tetrahydrofuran / 1 h / Ambient temperature 2: 1.) AcONa / ethanol / 0.5 h 3: NaBH3CN / ethanol / 3 h 4: H2 / 10percent Pd/C / ethanol 5: 2.) conc. aq. NH3 / 1.) EtOH, RT, overnight, 2.) EtOH, RT, 30 min
  • 22
  • [ 14683-47-7 ]
  • [1-{5-[3-(Benzhydryl-methyl-carbamoyl)-propoxy]-2-nitro-phenyl}-meth-(E)-ylidene]-amino}-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Na2CO3 / tetrahydrofuran / 1 h / Ambient temperature 2: 1.) AcONa / ethanol / 0.5 h
  • 23
  • [ 14683-47-7 ]
  • {5-[3-(Benzhydryl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq. Na2CO3 / tetrahydrofuran / 1 h / Ambient temperature 2: 1.) AcONa / ethanol / 0.5 h 3: NaBH3CN / ethanol / 3 h
  • 24
  • [ 23728-68-9 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / tetrahydrofuran / -78 deg C then warming to room temp. 2: 60 percent / LiAlH4 / tetrahydrofuran
  • 25
  • [ 591-51-5 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / tetrahydrofuran / -78 deg C then warming to room temp. 2: 60 percent / LiAlH4 / tetrahydrofuran
  • 26
  • [ 14683-47-7 ]
  • N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl(diphenylmethyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
S.8 Synthesis Example 8 Synthesis Example 8 N-(diphenylmethyl)methylamine (2.0 g) was processed in a similar manner as in Synthesis Example 5, whereby 2.90 g of N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl(diphenylmethyl)amine (Compound 11) were obtained. It was processed in a similar manner as in Synthesis Example 1, whereby 2.10 g of its hydrochloride were obtained as white crystals (yield: 61.5%). Melting point: 222-224° C. The following is its NMR spectrum data: 1 H-NMR (CDCl3,δ ppm): 1.26(9H,s), 2.68(3H,d), 3.64(1H,m), 3.86(1H,m), 4.85(1H,d), 5.71(1H,d), 6.10(1H,dt), 7.28-7.5(6H,m), 7.87(4H,m), 13.21(1H,br).
  • 27
  • [ 56146-83-9 ]
  • [ 14683-47-7 ]
  • methyl (N-diphenylmethyl-N-methylsulfamoyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% (a) Methyl (N-diphenylmethyl-N-methylsulfamoyl)acetate The subtitle compound (3.05 g, 37%) was prepared as a clear brown oil from N-methyl benzhydrylamine (prepared according to the method of Z. Horii, T Sakai and Inoi, Pharm Bull., 1955, 3, 159) (10.7 g, 50.7 mmol) and methyl chlorosulfonylacetate (4.27 g, 24.7 mmol), using the method of Example 1(a). 1H NMR (300 MHz, CDCl3) delta=2.84 (3H, s), 3.72 (3H, s), 3.82 (2H, s), 6.43 (1H, s) 7.10-7.47(10H, m). Found: C, 61.29; H 5.74; N, 4.21. C17H19O4NS requires C, 61.24; H 5.74; N, 4.20%.
  • 28
  • [ 14683-47-7 ]
  • [ 105-36-2 ]
  • [ 137075-18-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile for 2h; Heating / reflux; 1.A Example 1; Synthesis of Acetic Acid Intermediates; A. Synthesis of 2-(benzhvdryl(methyl)amino)acetic acid; 0077] To a solution of N-diphenylmethyl-methylamine 1.97g (10 mmol) in acetonitrile (20 ml) was added ethyl bromoacetate 1.2 ml (11 mmol) and potassium carbonate 1.38g (10 mmol). The reaction mixture was refluxed for two hours, concentrated, water was added and the product was then extracted with ethyl acetate 50 ml. The organic solution was dried over sodium sulfate and concentrated to give 3 g of crude ester. To the ester, lithium hydroxide 1.25 g (30 mmol) and methanol (10 ml), THF (30 ml) and water (10 ml) was added. The mixture was stirred at room temperature overnight, concentrated to remove solvent, neutralized with 2N HCl to pH~3, and extracted with ethyl acetate (40 ml). The organic layer was dried over sodium sulfate and concentrated to give 2.2g of desired product.
  • 29
  • [ 14683-47-7 ]
  • [ 4049-97-2 ]
  • [ 100288-45-7 ]
YieldReaction ConditionsOperation in experiment
31% With n-butyllithium In tetrahydrofuran; hexane n-BuLi in C6H14 was added to a soln. of N-(diphenylmethylen)methylamin in THF (solvents dry, N2-satd., -80 °C under N2); after 40 min, C2H3Ge(Ph)3 in THF was added dropwise at -50 °C; after 48 h warming to 0 °C, hydrolysis (H2O);; after extn. with ether (3 times), the organic phase was dried over Na2SO4 and concd.; chromy. of the residue on SiO2, eluent ethyl acetate/benzine 1:5, 1 st fraction excess educt, 2 nd fraction product; elem. anal.;;
  • 30
  • [ 32315-10-9 ]
  • [ 1187856-38-7 ]
  • [ 14683-47-7 ]
  • [ 1187856-37-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; N-(diphenylmethyl)methylamine With triethylamine In dichloromethane at 40℃; for 3h; Stage #2: tert-butyl 2-(((1r,4r)-4-(aminomethyl)cyclohexyl)methoxy)acetate In dichloromethane Reflux; 1.17 Example 1.17: Preparation of 2-(((lr,4r)-4-((3-Benzhydryl-3- methylureido)methyl)cyclohexyl)methoxy)acetic Acid (Compound 48).; A solution of N-methyl-1, 1 -diphenylmethanamine (25 mg, 0.127 mmol), triphosgene (41.4 mg, 0.139 mmol), triethylamine (0.088 mL, 0.634 mmol) in DCM (5 mL) was refluxed at 40 0C for 3 h. tert-Butyl 2-(((lr,4r)-4-(aminomethyl)cyclohexyl)methoxy)acetate (48.9 mg, 0.190 mmol) was added. The reaction mixture was refluxed overnight, quenched with H2O, and extracted with DCM. The organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by preparative LCMS to provide the title compound as a white solid (7.6 mg). LCMS m/z = 425.2 [M+H]+; 1H νMR (400 MHz, CDCl3) δ ppm 0.82-1.02 (m, 4H), 1.41 (m, IH), 1.57 (m, IH), 1.70 (d, J = 10.36 Hz, 2H), 1.80 (d, J = 10.36 Hz, 2H), 2.72 (s, 3H), 3.11 (t, J = 5.68 Hz, 2H), 3.36 (d, J = 6.32 Hz, 2H), 4.06 (s, 2H), 4.53 (m, IH), 6.64 (s, IH), 7.19 (d, J = 7.07 Hz, 4H), 7.27-7.38 (m, 6H).
  • 31
  • [ 74124-79-1 ]
  • [ 1187856-42-3 ]
  • [ 14683-47-7 ]
  • C29H39NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: di(succinimido) carbonate; tert-butyl 2-(((1r,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)acetate With triethylamine In dichloromethane at 20 - 80℃; Stage #2: N-(diphenylmethyl)methylamine With triethylamine In dichloromethane at 60℃; for 2h; microwave irradiation; 1.100 Example 1.100: Preparation of 2-(((lr,4r)-4-((Benzhydryl(methyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetic Acid (Compound 86).; To tert-butyl 2-(((lr,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)acetate (15 mg, 0.058 mmol) in DCM (0.5 mL) was added bis(2,5-dioxopyrrolidin-l-yl) carbonate (15.62 mg, 0.061 mmol) followed by TEA (0.016 mL, 0.116 mmol). The suspension was heated until the solution turned clear. The reaction was then stirred for 2 h at room temperature, followed by 2 h at 80 0C. N-methyl-l,l-diphenylmethanamine (17.18 mg, 0.087 mmol) and TEA (0.016 mL, 0.116 mmol) were added to the reaction mixture and the resulting solution was heated under microwave irradiation at 60 0C for 2 h. The organic solvent was evaporated and the residue was purified by preparative LCMS to provide an intermediate which was treated with 4.0 M HCl in dioxane for 1 h at 60 0C. The acid solution was evaporated and the residue was purified by preparative LCMS to provide the title compound as an oil (1.0 mg). LCMS m/z = 426.3 [M+H]+.
  • 32
  • [ 15761-38-3 ]
  • [ 14683-47-7 ]
  • [ 1186602-35-6 ]
YieldReaction ConditionsOperation in experiment
87% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; Inert atmosphere;
  • 33
  • [ 14683-47-7 ]
  • [ 7693-46-1 ]
  • [ 1209468-74-5 ]
YieldReaction ConditionsOperation in experiment
39% With triethylamine In dichloromethane for 2h; Inert atmosphere;
  • 34
  • [ 201230-82-2 ]
  • (E/Z)-1-(4-methoxyphenyl)prop-1-en-2-yl 4-methylbenzensulfonate [ No CAS ]
  • [ 14683-47-7 ]
  • (Z)-N-benzhydryl-3-(4-methoxyphenyl)-N,2-dimethylacrylamide [ No CAS ]
  • [ 1293370-73-6 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; palladium diacetate In toluene at 100℃; for 14h; Inert atmosphere; Molecular sieve; optical yield given as %de;
  • 36
  • [ 62965-35-9 ]
  • [ 14683-47-7 ]
  • [ 1200405-67-9 ]
YieldReaction ConditionsOperation in experiment
99% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; Inert atmosphere;
91% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; 1 (S)-tert-butyl 1-(benzhydryl(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (S)-tert-butyl 1-(benzhydryl(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate An oven-dried 50-mL round-bottomed flask was charged with Boc-L-tert-leucine (5) (2.78 g, 12.0 mmol, 1.0 equiv), HBTU (5.01 g, 13.2 mmol, 1.1 equiv), and N-(diphenylmethyl)methylamine (3.55 g, 18 mmol, 1.5 equiv). Anhydrous CH2Cl2 (24 mL) and N,N-diisopropylethylamine (4.18 mL, 24 mmol, 2.0 equiv) were added sequentially via syringe. The flask was capped with a plastic stopper, and the reaction mixture was stirred for 3 days at room temperature. The resulting orange mixture was diluted with Et2O (100 mL), washed with 1 N HCl (2*100 mL), sat. NaHCO3 (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure to provide a viscous orange oil. The product was subjected to purification by flash column chromatography on silica gel (gradient elution, 19:1→1:1 hexanes/Et2O, 100 g silica gel, 1.2 L solvent) to provide the product (6a) as a white foam (4.51 g, 11.0 mmol, 91% yield). [α]D25=-28.2° (c 1.76, CHCl3).The compound exists as a 5:1 mixture of amide rotamers in CDCl3. 1H NMR (500 MHz, CDCl3), major rotamer: δ 7.38-7.14 (11H, m), 5.28 (1H, d, J=10.0 Hz), 4.57 (1H, d, J=10.0 Hz), 2.97 (3H, s), 1.46, (9H, s), 1.03 (9H, s); minor rotamer: δ 7.38-7.14 (10H, m), 6.77 (1H, s), 5.28 (1H, d, J=10.0 Hz), 4.72 (1H, d, J=10.0 Hz), 2.73, (3H, s), 1.44 (9H, s), 0.93 (9H, s). 13C {1H} NMR (126 MHz, CDCl3), major rotamer: δ 173.0, 156.2, 139.3, 138.4, 129.4, 128.5, 128.4, 127.9, 127.6, 127.1, 79.6, 60.8, 56.7, 35.2, 33.2, 28.3, 26.5; minor rotamer: δ 173.5, 155.5, 139.4, 138.8, 129.0, 128.5, 128.4, 128.3, 127.7, 127.6, 79.5, 64.6, 56.1, 35.3, 31.3, 28.3, 26.5. IR (cm-1): 3436 (w), 3326 (w), 3062 (w), 3029 (w), 2965 (m), 2871 (w), 1953 (w), 1893(w), 1810 (w), 1712 (s), 1640 (s), 1496 (s), 1454 (m), 1404 (m), 1366 (m), 1320 (w), 1245 (m), 1172 (s), 1105 (w), 1058 (w), 1005 (w), 974 (w), 922 (w), 870 (w), 734 (w), 702 (m), 608 (w). LRMS (ESI): 433.25 (100%) [M+Na]+.
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;
  • 37
  • [ 14683-47-7 ]
  • [ 1421697-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 38
  • [ 14683-47-7 ]
  • [ 1421697-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 39
  • [ 14683-47-7 ]
  • [ 1421697-50-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 40
  • [ 14683-47-7 ]
  • [ 1421697-58-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere
  • 41
  • [ 14683-47-7 ]
  • [ 1421697-60-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 42
  • [ 14683-47-7 ]
  • (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3-dimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 43
  • [ 14683-47-7 ]
  • [ 1186602-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 44
  • [ 14683-47-7 ]
  • [ 1186602-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 2: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
  • 45
  • [ 14683-47-7 ]
  • [ 1421697-44-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 46
  • [ 14683-47-7 ]
  • [ 1421052-39-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere 3: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 47
  • [ 13734-41-3 ]
  • [ 14683-47-7 ]
  • [ 1421697-56-4 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; Inert atmosphere;
  • 48
  • [ 14683-47-7 ]
  • [ 1427203-61-9 ]
  • [ 1427204-05-4 ]
YieldReaction ConditionsOperation in experiment
56% With tetra-(n-butyl)ammonium iodide; potassium carbonate In tetrahydrofuran for 7h; Reflux;
  • 49
  • [ 14683-47-7 ]
  • [ 1186602-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 20 °C 2: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3: dichloromethane / 2 h / 20 °C
  • 51
  • [ 14683-47-7 ]
  • [ 563-76-8 ]
  • [ 1613244-31-7 ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine In dichloromethane at -40 - 20℃; for 4h;
  • 52
  • [ 14683-47-7 ]
  • [ 65638-93-9 ]
  • C25H26N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 7.5h;
  • 53
  • [ 14683-47-7 ]
  • [ 1613244-32-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / -40 - 20 °C 2: potassium hydrogencarbonate / acetonitrile / 18 h / 20 °C / Reflux
  • 54
  • [ 14683-47-7 ]
  • [ 65095-13-8 ]
  • N-benzhydryl-N-methyl-1H-benzo[d][1,2,3]triazole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In toluene at 20℃; for 1h; 2.1.2. 1-(N-arylcarbamoylbenzotriazoles (1-benzotriazoleamides)(2a-d): general procedure General procedure: The title compounds were synthesized from chloride 1 and corresponding amine or hydrazone according to slightly modified published procedure [19]. Solution of 1.515 g (15.0 mmol) TEA and 5.0 mmol of amine or hydrazone in 5 ml toluene was added dropwise to a solution of 0.908 g (5.0 mmol) BtcCl (1) in dry toluene (10 ml). Reaction mixture was stirred 1 h at room temperature, extracted with 5% NaOH solution (3 x 15 ml) and water (3 x 15 ml). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure.
  • 55
  • [ 14683-47-7 ]
  • N-benzhydryl-2-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-N-methylhydrazinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / toluene / 1 h / 20 °C 2: hydrazine / 1,4-dioxane / 25 h / 20 °C 3: triethylamine / 1,4-dioxane / 1 h / 15 °C
  • 56
  • [ 14683-47-7 ]
  • N-benzhydryl-N-(4-((6-metoxyquinolin-8-yl)amino)pentyl)-N-methylhydrazine-1,2-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / toluene / 1 h / 20 °C 2: hydrazine / 1,4-dioxane / 25 h / 20 °C 3: triethylamine / 1,4-dioxane / 1 h / 15 °C 4: sodium dithionite; triethylamine / 1,4-dioxane / 18.5 h / 20 °C / Darkness
  • 57
  • [ 14683-47-7 ]
  • ethyl N-benzhydryl-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / toluene / 1 h / 20 °C 2: ethanol / 1 h / 20 °C
  • 58
  • [ 14683-47-7 ]
  • N-benzhydryl-N-methylhydrazinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / toluene / 1 h / 20 °C 2: hydrazine / 1,4-dioxane / 25 h / 20 °C
  • 59
  • [ 1042740-40-8 ]
  • [ 14683-47-7 ]
  • 1-benzhydryl-3-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-1-methylurea [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With sodium dithionite; triethylamine In dichloromethane at 65℃; Microwave irradiation; Darkness; 2.1.8. Ureas 9a-g: general procedure General procedure: Method A: A solution of 0.162 g (0.4 mmol) primaquine benzotriazolide 8, 0.061 g (0.6 mmol) TEA and 0.6 mmol corresponding amine in dichloromethane (2 ml) was heated at 65 oC in microwave reactor for 60-80 min. The reaction mixture was extracted with 5% NaOH solution (3 x 10 ml) and water (3 x 15 ml), dried over anhydrous sodium sulfate and evaporated. Additional 0.4 mmol of TEA was added if the reaction started from amine salt. The reaction with primaquine was run light protected in the presence of few milligrams of sodium dithionite.
  • 60
  • [ 14683-47-7 ]
  • 2-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazinecarboxamide [ No CAS ]
  • N-benzhydryl-N-(4-((6-metoxyquinolin-8-yl)amino)pentyl)-N-methylhydrazine-1,2-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine In 1,4-dioxane 2.1.7. 1-Primaquinecarbonyl-4-substituted semicarbazides (7a-l): general procedure General procedure: Method B: A solution of 0.5 mmol amine or amine salt and 0.101 g (1 mmol) TEA in dioxane or dichloromethane (6 ml) was added drop-wise to a solution of 0.232 g (0.5 mmol) compound 11 in dioxane (6 ml). The reaction mixture was stirred 2-20 h, the solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (10 ml) and extracted with 5% NaOH solution (3 x 10 ml) and water (3 x 15 ml), dried over anhydrous sodium sulfate and evaporated.
  • 61
  • [ 67-56-1 ]
  • [ 1013-88-3 ]
  • [ 14683-47-7 ]
  • [ 5336-72-1 ]
  • [ 91-00-9 ]
YieldReaction ConditionsOperation in experiment
1: 34% 2: 20% 3: 20% With C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Sealed tube; Inert atmosphere;
  • 62
  • N-(benzhydryl)ammonium 2,3,3,3-tetrafluoro-2-methoxypropanoate [ No CAS ]
  • [ 10186-64-8 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water for 0.5h; Inert atmosphere; 4.2. Liberation of the acid 10 and the amines 2a-2c, 6a-6c, 7a, 7c and11 from the salts 4a-4c, 5a, 5c and 8 General procedure: About 50 mg of a salt was diluted in 1 mL of water, and 1 mL of conc. HCl was added. After 30 min of stirring, the mixture was extracted by 2 × 2 mL of diethyl ether. The organic part was dried over MgSO4 and analysed by GC-MS. In all cases, only propionic acid 10 was detected. The aqueous part was neutralized with solid K2CO3 and basified to pH 10 with conc. aqueous KOH. The mixture was extracted with 2 × 2 mL of diethyl ether, combined organic fractions were dried over MgSO4 and analysed by GC-MS to identify the base parts of the salts (the spectral characteristics were in accord with database values). Aniline (2a): MS (EI+): 93 (100) [M+], 66 (44), 65 (26), 39 (18). N-methylaniline (6a): MS (EI+): 107 (75) [M+], 106 (100), 77 (24), 65 (8), 51 (14), 39 (8). N,N-dimethylaniline (7a): MS (EI+): 121 (67) [M+], 120 (100), 104 (16), 91 (4), 77 (25), 51 (16), 42 (10).
  • 63
  • N-benzhydryl-N-methylpicolinamide [ No CAS ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: N-benzhydryl-N-methylpicolinamide With hydrogenchloride In water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With zinc In water at 20℃; for 16h; Inert atmosphere; 4. General Procedure for Picolinamide Cleavage UsingZn/HCl in Water General procedure: To a suspension of the starting picolinic amide (0.15 mmol, 1.0 equiv) in H2O(3 mL) was added 12M HCl (0.37 mL) and the mixture was stirred for 5 minutes atrt. Zinc dust (145 mg, 2.24 mmol, 15 equiv) was then added in three portionsand the mixture was stirred at rt. After 16 h, the reaction was mixed with ca. 200 mg of sand (to assistfiltration) and filtered through a celite plug. The filtrate was transferred toa separating funnel with 2M NaOH (50 mL) and extracted twice with DCM (2 x 50 mL).The combined organic phase was dried over Na2SO4 and theyield was analysed by 1H NMR via the addition of 1,3,5-trimethoxybenzene (0.33equiv) as an internal standard. The crude mixture was then purified bypreparative TLC using MeOH/DCM. Characterisation data were in agreement withliterature values.
  • 64
  • [ 98-98-6 ]
  • [ 14683-47-7 ]
  • N-benzhydryl-N-methylpicolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h; Inert atmosphere; 2. General Procedure for Picolinamide Formation General procedure: HATU(1.00 g, 2.63 mmol, 1.05 equiv) was added to a stirred solution of the startingamine (2.50 mmol, 1.0 equiv), N,N-diisopropylethylamine(1.30 mL, 7.55 mmol, 3.0 equiv) and picolinic acid (325 mg, 2.63 mmol,1.05 equiv) in methylene chloride (25 ml) and the mixture was stirred at roomtemperature overnight. In the morning, the reaction mixture was transferred toseparating funnel with 25 mL H2O and extracted twice with methylenechloride (2 x 25 mL). The combined organic phase was dried over Na2SO4,filtered and solvents were removed invacuo. The residue was purified by column chromatography over silica gelusing gradient elution (40 to 100% Et2O in hexane).
  • 65
  • [ 14683-47-7 ]
  • [ 15486-96-1 ]
  • 3-bromo-N-(diphenylmethyl)-N-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; General procedure (A) for the preparation of 3-bromo-N-substituted- and 3-bromo-N,N-disubstituted propanamide derivatives (1-3) General procedure: To a solution of bromoacetyl chloride (1.40g, 8.17mmol) in10mL of dry THF cooled at 0°C, under argon atmosphere, was added dropwise, under vigorous stirring, a solution of the appropriate amine (5.45mmol) and triethylamine (0.276g, 2.72mmol) in dry THF (10mL). After 30min at 0° and 30min at room temperature the reaction mixture was quenched by the addition of 50ml of H2O and extracted with dichloromethane (3×50ml). The combined organic extracts were washed with saturated NaHCO3 and brine, and then dried over anhydrous Na2SO4. Evaporation under reduced pressure gave the crude 3-bromopropanamide derivatives (1-3) which were purified by flash chromatography on silica gel, using CH2Cl2 and cyclohexane as eluent.
  • 66
  • [ 14683-47-7 ]
  • N-(diphenylmethyl)-3-[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]-N-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: sodium hydrogencarbonate; potassium iodide / methanol / 24 h / 50 °C / Inert atmosphere; Darkness
  • 67
  • [ 14683-47-7 ]
  • C24H26N4O12*C55H70O10 [ No CAS ]
  • C55H70O10*C40H48N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With triethylamine In chloroform Reflux; Inert atmosphere;
  • 68
  • [ 4834-98-4 ]
  • [ 1392006-73-3 ]
  • [ 14683-47-7 ]
  • C55H70O10*C40H48N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1,12-dodecanedioyl dichloride; 1,4-bis(ethoxy)pillar[5]arene In chloroform at -15℃; for 1.5h; Inert atmosphere; Stage #2: N-(diphenylmethyl)methylamine With triethylamine In chloroform at -15 - 20℃; Inert atmosphere;
  • 69
  • [ 14683-47-7 ]
  • [ 7154-66-7 ]
  • N-benzhydryl-2-bromo-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In dichloromethane at 0 - 20℃;
  • 70
  • [ 14683-47-7 ]
  • 6-methyl-7-phenyl-6,7-dihydrodibenzo[d,f][1,2]thiazepine 5,5-dioxide [ No CAS ]
  • 6-methyl-7-phenyl-6,7-dihydrodibenzo[d,f][1,2]thiazepine 5,5-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; (R)-2-((2'-(bis(3,5-dimethylphenyl)phosphaneyl)-[1,1'-binaphthalen]-2-yl)oxy)acetic acid / 1,2-dimethoxyethane / 48 h / 140 °C / Inert atmosphere; Molecular sieve
  • 71
  • [ 14683-47-7 ]
  • 6-methyl-7-phenyl-6,7-dihydrodibenzo[d,f][1,2]thiazepine 5,5-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: caesium carbonate; Trimethylacetic acid; tricyclohexylphosphine tetrafluoroborate; palladium diacetate / 5,5-dimethyl-1,3-cyclohexadiene / 140 °C / Sealed tube; Inert atmosphere
  • 72
  • [ 14683-47-7 ]
  • [ 2905-25-1 ]
  • N-benzhydryl-2-bromo-N-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine In dichloromethane at 0 - 20℃;
  • 73
  • [ 14683-47-7 ]
  • C15H11ClN4O2 [ No CAS ]
  • 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-N-(diphenylmethyl)-N-methyl-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.857 g With triethylamine In toluene at 20℃; for 0.5h; 4.1.4 Btc-amino acid amides (9a-g): general procedure General procedure: A solution of 3.4mmol corresponding amine or hydrazone and 4mmol 78 TEA in dry 75 toluene (20ml) was added dropwise to a solution of 4mmol chloride 8 in dry toluene (30ml). The reaction mixture was stirred 30minat room temperature. TEA×HCl was filtered off and mother liquor was evaporated. The residue was dissolved in 79 ethyl acetate/1% 80 HCl mixture (1:1). The organic layer was extracted three times with HCl solution (w=1%), washed two times with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure.
  • 74
  • [ 119-61-9 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: titanium(IV) isopropylate / toluene / 80 °C / Inert atmosphere 2: (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-Methyldicyclohexylamine / acetonitrile / 15 - 20 °C / Inert atmosphere; Sealed tube; Irradiation
  • 75
  • [ 14683-47-7 ]
  • (S)-N-benzhydryl-2-{{2-[3,5-bis(trifluoromethyl)phenyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C 3: triethylamine / dichloromethane / 48 h / 20 °C
  • 76
  • [ 14683-47-7 ]
  • (R)-N-benzhydryl-2-{{2-[3,5-bis(trifluoromethyl)phenyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C 3: triethylamine / dichloromethane / 48 h / 20 °C
  • 77
  • [ 14683-47-7 ]
  • (S)-N-benzhydryl-2-{{2-[3,5-bis(trifluoromethyl)phenyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N-methyl-3-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C 3: triethylamine / dichloromethane / 48 h / 20 °C
  • 78
  • [ 14683-47-7 ]
  • (S)-N-benzhydryl-2-{{3,4-dioxo-2-[(perfluorophenyl)amino]cyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C 3: triethylamine / dichloromethane / 48 h / 20 °C
  • 79
  • [ 14683-47-7 ]
  • (S)-N-benzhydryl-2-{{2-[3,5-bis(trifluoromethyl)benzyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C 3: triethylamine / dichloromethane / 48 h / 20 °C
  • 80
  • [ 14683-47-7 ]
  • (S)-2-amino-N-benzhydryl-N,3,3-trimethylbutanamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C
  • 81
  • [ 14683-47-7 ]
  • C23H24N2O*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C
  • 82
  • [ 14683-47-7 ]
  • C20H26N2O*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; water / 2 h / 0 - 20 °C
  • 83
  • [ 14683-47-7 ]
  • [ 13734-34-4 ]
  • C28H32N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;
  • 84
  • [ 1070-83-3 ]
  • [ 14683-47-7 ]
  • N-benzhydryl-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;
  • 85
  • [ 14683-47-7 ]
  • [ 124655-17-0 ]
  • C25H34N2O3 [ No CAS ]
  • 86
  • [ 6773-29-1 ]
  • [ 14683-47-7 ]
  • C18H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90 % ee With (S)-2'-(bis(3,4,5-trifluorophenyl)phosphoryl)-3-(3,5-di-tert-butyl-4-methoxyphenyl)-[1,1'-binaphthalene]-2-carboxylic acid; silver carbonate In methanol at 60℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; enantioselective reaction;
  • 87
  • [ 14683-47-7 ]
  • (R)-2-methyl-1-phenyl-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silver carbonate; (S)-2'-(bis(3,4,5-trifluorophenyl)phosphoryl)-3-(3,5-di-tert-butyl-4-methoxyphenyl)-[1,1'-binaphthalene]-2-carboxylic acid / methanol / 18 h / 60 °C / Inert atmosphere; Glovebox; Sealed tube 2: lithium chloride; water / dimethyl sulfoxide / 3 h / 130 °C / Inert atmosphere
  • 88
  • [ 14683-47-7 ]
  • [ 18531-94-7 ]
  • N-benzhydryl-N-methyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: N-(diphenylmethyl)methylamine With triethylamine; phosphorus trichloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; Stage #2: (R)-1,1'-Bi-2-naphthol In dichloromethane at 20℃; Inert atmosphere;
  • 89
  • [ 14683-47-7 ]
  • C12H20Cl2O2*C55H70O10 [ No CAS ]
  • C55H70O10*C40H48N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In neat (no solvent) for 2h; Milling;
  • 90
  • [ 32315-10-9 ]
  • [ 14683-47-7 ]
  • [ 1187857-68-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃; for 6h; General procedures for carbamoyl chloride formation and enantioselective palladium-catalyzed cyclization General procedure: To a solution of amine 1 (0.2 mmol, 1.0 equiv) and trimethylamine(0.086 mL, 3.0 equiv) in dichloroethane (2.0 mL) at 0 C was added dropwise a solution of triphosgene solution (0.2 mmol in2mL DCM). The mixture was allowed to warm to rt and stirred for 6 h. Saturated sodium bicarbonate solution (20 mL) was added to quench this reaction. The organic layer was separated and the aqueous phasewas extracted with dichloroethane for 3 times (2 mLX 3). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was use ddirectly for the next step without any further purification. To the mixture of Pd(OAc)2 (0.4 mg, 1 mol %), (R)-AntPhos (3.0 mg, 4 mol%), PivOH (7.0 mg, 30 mol %), Cs2CO3 (66 mg, 1.0 equiv) and substrate 2 (~0.2 mmol)was added toluene (2 mL) in the glove box. The mixture was then transferred to an autoclave and charged with CO pressure (9 atm). The mixture was stirred at 80 C for 24 h. Water (2 mL) was added to the mixture to quench the reaction. The organic layer was separated and the aqueous phase was extracted with EtOAc (2 mL X 3). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography to give product 3, whose enatiomeric excess was determined by chiral HPLC.
  • 91
  • [ 124-38-9 ]
  • [ 14683-47-7 ]
  • benzhydryl(methyl)carbamic fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; for 2h; Schlenk technique;
  • 92
  • [ 14683-47-7 ]
  • [ 18531-99-2 ]
  • N-benzhydryl-N-methyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: N-(diphenylmethyl)methylamine With triethylamine; phosphorus trichloride In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: (S)-[1,1']-binaphthalenyl-2,2'-diol In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;
  • 93
  • [ 3376-23-6 ]
  • [ 100-58-3 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
70 mg Stage #1: N-methyl-α-phenylnitrone; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With indium; ammonium chloride; zinc In tetrahydrofuran; ethanol; water Reflux;
  • 94
  • [ 14683-47-7 ]
  • (E)-2-diazo-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-3-en-1-one [ No CAS ]
  • (R,E)-4-(benzhydryl(methyl)amino)-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-2-en-1-one [ No CAS ]
  • (R,Z)-4-(benzhydryl(methyl)amino)-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 58% With cobalt(II) trifluoromethanesulfonate; C31H44N4O4 In chloroform at 50℃; for 0.166667h; stereoselective reaction;
  • 95
  • [ 14683-47-7 ]
  • (E)-2-diazo-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-3-en-1-one [ No CAS ]
  • 4-(benzhydryl(methyl)amino)-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cobalt(II) trifluoromethanesulfonate; C38H58N4O4 In chloroform at 50℃;
  • 96
  • [ 32315-10-9 ]
  • [ 14683-47-7 ]
  • [ 87-62-7 ]
  • 1-benzhydryl-3-(2,6-dimethylphenyl)-1-methylurea [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: bis(trichloromethyl) carbonate; 2,6-dimethylaniline With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Inert atmosphere; Stage #2: N-(diphenylmethyl)methylamine With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Inert atmosphere;
  • 98
  • [ 1223105-85-8 ]
  • [ 14683-47-7 ]
  • [ 124655-17-0 ]
  • (R)-N-benzhydryl-2-{{2-[3,5-bis(trifluoromethyl)phenyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.25h; Stage #2: N-(diphenylmethyl)methylamine In dichloromethane at 20 - 23℃; for 12h; Stage #3: 3-(3,5-ditrifluoromethylphenylamino)-4-methoxybutane-3-en-1,2-dione Further stages;
  • 99
  • [ 15761-39-4 ]
  • [ 14683-47-7 ]
  • C24H30N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: N-(diphenylmethyl)methylamine In dichloromethane at 20℃; Inert atmosphere;
  • 100
  • [ 14683-47-7 ]
  • C19H22N2O*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; water monomer; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
  • 101
  • [ 14683-47-7 ]
  • C28H25F6N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; water monomer; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 3.2: 48 h / 20 °C / Inert atmosphere
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