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[ CAS No. 177976-49-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 177976-49-7
Chemical Structure| 177976-49-7
Chemical Structure| 177976-49-7
Structure of 177976-49-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 177976-49-7 ]

CAS No. :177976-49-7 MDL No. :MFCD00270124
Formula : C13H13N Boiling Point : -
Linear Structure Formula :- InChI Key :WKHABRRJMGVELW-UHFFFAOYSA-N
M.W :183.25 Pubchem ID :2760368
Synonyms :

Calculated chemistry of [ 177976-49-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.55
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 3.06
Log Po/w (WLOGP) : 2.66
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 2.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.41
Solubility : 0.0719 mg/ml ; 0.000392 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.0977 mg/ml ; 0.000533 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00201 mg/ml ; 0.000011 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 177976-49-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3259
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 177976-49-7 ]

* 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 [ 177976-49-7 ]

[ 177976-49-7 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 858443-07-9 ]
  • [ 177976-49-7 ]
  • 2
  • [ 177976-49-7 ]
  • <i>N</i>-(3-phenyl-benzyl)-acetamide [ No CAS ]
  • 3
  • [ 177976-49-7 ]
  • [ 100-52-7 ]
  • benzylidene-(3-phenyl-benzyl)-amine [ No CAS ]
  • 4
  • [ 177976-49-7 ]
  • [ 153527-28-7 ]
  • (2R,3S,5R)-5-{2-[(Biphenyl-3-ylmethyl)-amino]-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol [ No CAS ]
  • 5
  • [ 177976-49-7 ]
  • [ 203922-22-9 ]
  • [ 203922-25-2 ]
  • 6
  • [ 1204-60-0 ]
  • [ 177976-49-7 ]
  • 7
  • [ 177976-49-7 ]
  • [ 224773-81-3 ]
  • <i>N</i>-biphenyl-3-ylmethyl-2-[2-(4-fluoro-benzylsulfanyl)-4-oxo-5-pyrimidin-5-ylmethyl-4<i>H</i>-pyrimidin-1-yl]-acetamide [ No CAS ]
  • 8
  • [ 177976-49-7 ]
  • [3-<i>tert</i>-butoxycarbonylmethyl-2-(2,4-dichloro-phenyl)-4-oxo-thiazolidin-5-yl]-acetic acid [ No CAS ]
  • [5-[(biphenyl-3-ylmethyl)-carbamoyl]-methyl}-2-(2,4-dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-acetic acid <i>tert</i>-butyl ester [ No CAS ]
  • 9
  • [ 869277-22-5 ]
  • [ 177976-49-7 ]
  • AQ903091 [ No CAS ]
  • 10
  • [ 29684-56-8 ]
  • [ 632-46-2 ]
  • [ 177976-49-7 ]
  • <i>N</i>-biphenyl-3-ylmethyl-2,6-dimethyl-benzamide [ No CAS ]
  • 1-biphenyl-3-ylmethyl-3-(2,6-dimethyl-benzoyl)-urea [ No CAS ]
  • 11
  • [ 110-62-3 ]
  • [ 177976-49-7 ]
  • Biphenyl-3-ylmethyl-pent-(Z)-ylidene-amine [ No CAS ]
  • 12
  • [ 29684-56-8 ]
  • [ 177976-49-7 ]
  • [ 99-06-9 ]
  • <i>N</i>-biphenyl-3-ylmethyl-3-hydroxy-benzamide [ No CAS ]
  • 1-biphenyl-3-ylmethyl-3-(3-hydroxy-benzoyl)-urea [ No CAS ]
  • 13
  • [ 29684-56-8 ]
  • [ 177976-49-7 ]
  • [ 75-98-9 ]
  • <i>N</i>-biphenyl-3-ylmethyl-2,2-dimethyl-propionamide [ No CAS ]
  • 1-biphenyl-3-ylmethyl-3-(2,2-dimethyl-propionyl)-urea [ No CAS ]
  • 14
  • [ 919995-76-9 ]
  • [ 177976-49-7 ]
  • 2-benzyl-<i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-malonamide [ No CAS ]
  • 15
  • [ 914646-71-2 ]
  • [ 177976-49-7 ]
  • [ 914646-90-5 ]
  • 16
  • [ 919995-77-0 ]
  • [ 177976-49-7 ]
  • <i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-2-(4-fluoro-benzyl)-malonamide [ No CAS ]
  • 17
  • [ 919995-79-2 ]
  • [ 177976-49-7 ]
  • <i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-2-(1-methyl-1<i>H</i>-benzoimidazol-2-ylmethyl)-malonamide [ No CAS ]
  • 18
  • [ 919995-78-1 ]
  • [ 177976-49-7 ]
  • <i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-2-(3-phenoxy-benzyl)-malonamide [ No CAS ]
  • 19
  • {(2SR,5RS)-3-[3-(aminocarbonyl)phenyl]-2-[4-(benzyloxy)phenyl]-5-methyl-4-oxo-1,3-thiazolidin-5-yl}acetic acid [ No CAS ]
  • [ 177976-49-7 ]
  • 3-[(2SR,5RS)-2-[4-(benzyloxy)phenyl]-5-{2-[([1,1'-biphenyl-3-yl]methyl)amino]-2-oxoethyl}-5-methyl-4-oxo-1,3-thiazolidin-3-yl]benzamide [ No CAS ]
  • 20
  • 2-[(2SR,5RS)-3-[3-(aminocarbonyl)phenyl]-2-[4-(benzyloxy)phenyl]-5-methyl-4-oxo-1,3-thiazolidin-5-yl]ethyl 4-nitrophenyl carbonate [ No CAS ]
  • [ 177976-49-7 ]
  • 2-[(2SR,5RS)-3-[3-(aminocarbonyl)phenyl]-2-[4-(benzyloxy)phenyl]-5-methyl-4-oxo-1,3-thiazolidin-5-yl]ethyl N-([1,1'-biphenyl-3-yl]methyl)carbamate [ No CAS ]
  • 21
  • [ 177976-49-7 ]
  • [ 608520-21-4 ]
  • <i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-malonamide [ No CAS ]
  • 22
  • [ 177976-49-7 ]
  • [ 608520-22-5 ]
  • <i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-<i>tert</i>-butoxy-2-isobutyl-malonamide [ No CAS ]
  • 23
  • [ 177976-49-7 ]
  • [ 608520-24-7 ]
  • [(biphenyl-3-ylmethyl)-carbamoyl]-<i>tert</i>-butoxycarbamoyl-methyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 24
  • [ 177976-49-7 ]
  • [ 391680-92-5 ]
  • 5,6-dihydroxy-2-thiophen-2-yl-pyrimidine-4-carboxylic acid (biphenyl-3-ylmethyl)-amide [ No CAS ]
  • 25
  • [ 919995-82-7 ]
  • [ 177976-49-7 ]
  • 2-benzyl-<i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-trityloxy-malonamide [ No CAS ]
  • 26
  • (E)-3-[3-cyano-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid [ No CAS ]
  • [ 177976-49-7 ]
  • (E)-N-biphenyl-3-ylmethyl-3-[3-cyano-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; To a DMF (0.2 mL) solution of (E)-3-[3-cyano-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (15 mg) and <strong>[177976-49-7]3-phenylbenzylamine</strong> monohydrochloride (16 mg), TEA (0.007 mL), HOBT (10 mg) and EDC (14 mg) were added one by one, and the reaction mixture was agitated at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (Carrier:ChromatorexNH, elution solvent:hexane-ethyl acetate system), and 5 mg of the title compound was obtained. 1H-NMR (CDCl3) delta (ppm): 2.32 (s, 3H), 4.67 (d, J=6 Hz, 2H), 6.04-6.08 (m, 1H), 6.49 (d, J=15.6 Hz, 1H), 7.09 (s, 1H), 7.32-7.60 (m, 10H), 7.68 (d, J=15.6 Hz, 1H), 7.76-7.79 (m, 2H), 7.89 (d, J=2 Hz, 1H).
  • 27
  • sodium [(1,3-dioxoisoindolin-2-yl)methyl]trifluoroborate [ No CAS ]
  • [ 2113-57-7 ]
  • [ 177976-49-7 ]
YieldReaction ConditionsOperation in experiment
51% To the mixture of 3-bromobiphenyl (0.020 ml, 0.12 mmol) and 1,4-dioxane (1.5 nil), water (0.15 ml), potassium phosphate tribasic n-hydrate (170 mg, 0.72 mmol), sodium 1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl trifluoroborate (60 mg, 0.24 mmol), palladium(II) acetate (2.7 mg, 0.012 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (9.9 mg, 0.024 mmol) were added, and then the obtained reaction mixture was stirred at 94 C. (an outer temperature) overnight. The reaction mixture was cooled to room temperature, and then hydrazine hydrate (48 mg, 0.96 mmol) and methanol (2 ml) were added thereto, followed by heating to reflux for 40 min. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture, followed by filtration with celite. The organic layer of the filtrate was separated and washed with saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with NH-silica gel column chromatography (ethyl acetate), thereby obtaining the entitled compound (11 mg, 51%) as the mixture with 2'-(dicyclohexyl-phosphinoyl)-2,6-dimethoxy-biphenyl (6.2 mg). 1H-NMR Spectrum (CDCl3) delta(ppm): 3.95(2H, s), 7.30-7.37(2H, m), 7.40-7.50(4H, m), 7.54-7.55(1H, m), 7.59-7.61(2H, m)
  • 28
  • [ 177976-49-7 ]
  • N-(biphenyl-3-ylmethyl)-2-methyl-1-[(1-methyl-1H-benzimidazol-2-yl)thio]acetyl}-L-prolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 270 mg (0.78 mmol) 7^2 dissolved in 10 mL of 1 : 1 MeOeta/TetaF was added 1.2 mL (1.2 mmol) of IM LiOH. After stirring for 1.5 h, the temperature was increased to 45C and stirring was continued for 5 h, then the reaction was allowed to stand overnight at room temperature. To the mixture was added 1.5 mL IM HCl and the solvents were removed by rotary evaporation. The residue was dissolved in 10 mL DMF and to it was added 297 mg (1.6 mmol) <strong>[177976-49-7]3-phenylbenzylamine</strong>, 219 mg (1.6 mmol) 1-hydroxybenzotriazole hydrate, 340 muL (2.4 mmol) triethylamine, and finally 311 mg (1.6 mmol) EDC. The reaction was heated at 800C for 1.5 h, then partitioned between EtOAc and 5% aqueous Na2CO3. The layers were separated and the organic was washed with water, brine, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide crude 7-3. This material was then purified by RP etaPLC with Ceta3CN/eta2O (0.1% TFA), the fractions containing the desired material were free-based with NaHCtheta3, extracted into EtOAc, dried over Na2SO-J, and concentrated to provide 7^3 as a white solid. Data for 7^: LC/MS: rt = 2.01 min; m/z (M + H) = 499.1 , found; 499.2 required. 1H NMR (500 MHz5 CDCl3): delta 7.8 (m, IH), 7.55 (m, 2H), 7.45 - 7.25 (m, 5 H), 7.15 - 7.05 (m, 3H), 6.9 - 6.8 (m, 3H), 4.6 - 4.5 (m, 2H), 4.3 (m, IH), 3.8 (m, IH), 3.6 (m, 2H), 3.3 (s, 3H), 2.5 (m, IH), 2.2 - 2.0 (m, 3H), 1.8 (m, 3H) ppm. HRMS m/z (M+H) 499.2166 found; 499.2162 required.
  • 29
  • [ 177976-49-7 ]
  • [ 96989-50-3 ]
  • [ 2381-75-1 ]
  • 1-(4-chlorophenoxyacetyl)-4-(3-phenylbenzyl)-thiosemicarbazide [ No CAS ]
  • 30
  • [ 177976-49-7 ]
  • 2-benzyl-<i>N</i>-biphenyl-3-ylmethyl-<i>N</i>'-hydroxy-malonamide [ No CAS ]
  • 31
  • [ 177976-49-7 ]
  • 1-biphenyl-3-ylmethyl-5-butyl-4-(2-methoxy-phenyl)-1<i>H</i>-imidazole [ No CAS ]
  • 32
  • [ 643-93-6 ]
  • [ 177976-49-7 ]
  • 33
  • [ 14704-31-5 ]
  • [ 177976-49-7 ]
  • 34
  • N-(4-carbamimidoyl-phenyl)-2-phenyl-malonamic acid sodium salt [ No CAS ]
  • [ 177976-49-7 ]
  • CH2O2*C29H26N4O2 [ No CAS ]
  • 35
  • 1-(3-cyano-benzyl)-4-methyl-1H-indole-2-carboxylic acid [ No CAS ]
  • [ 177976-49-7 ]
  • [ 1027400-20-9 ]
  • 36
  • [ 638190-17-7 ]
  • [ 177976-49-7 ]
  • (2S)-3-(4-{1-[(biphenyl-3-ylmethyl)-carbamoyl]-1-methyl-ethoxy}-phenyl)-2-ethoxy-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was prepared from [(2S)-3- [4- (1-CARBOXY-1-METHYL-ETHOXY)-] phenyl] -2-ethoxy-propionic acid ethyl ester (EXAMPLE 49, step 2) and C-biphenyl-3-yl- methylamine via the same procedure used for the preparation of (2S, [LR)-2-ETHOXY-3- (4-] [{L- [2- (4-PHENOXY-PHENYL)-ETHYLCARBAMOYL]-ETHOXY}-PHENYL)-PROPIONIC] acid (Example 1, step 3) to produce a colorless oil. MS (ES) for [C28H3LNO5 [M-H]-:] 462.
  • 37
  • [ 638190-26-8 ]
  • [ 177976-49-7 ]
  • (2S)-3-(3-{1-[(biphenyl-3-ylmethyl)-carbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was prepared from [(2S)-3- [3- (1-CARBOXY-1-METHYL-ETHOXY)-] phenyl] -2-methoxy-propionic acid methyl ester (EXAMPLE 56, step 2) and C-biphenyl- [3-YL-METHYLAMINE] via the same procedure used for the preparation of (2S, [LR)-2-ETHOXY-] [3- {1-[2-(4-PHENOXY-PHENYL)-ETHYLCARBAMOYL]-ETHOXY}-PHENYL)-PROPIONIC ACID] (Example 1, step 3) to produce a colorless oil. MS (ES) for [C27H28NO5] [[M-H]- :] 446.
  • 38
  • [ 638189-65-8 ]
  • [ 177976-49-7 ]
  • (2S)-3-(4-{1-[(biphenyl-3-ylmethyl)-carbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was prepared from [(2S)-3- [4- ( 1-CARBOXY-1-METHYL-ETHOXY)-] phenyl] -2-methoxy-propionic acid ethyl ester (PREPARATION 5, step 2) and C- <strong>[177976-49-7]biphenyl-3-yl-methylamine</strong> via the same procedure used for the preparation of (2S, [1R)-] 2-ethoxy-3- [(4- {L- [2- (4-PHENOXY-PHENYL)-ETHYLCARBAMOYL]-ETHOXY}-PHENYL)-PROPIONIC] acid (Example 1, step 3) to produce a colorless oil. MS (ES) for [C27H29NO5] [[M-H]- :] 446.
  • 39
  • [ 638190-42-8 ]
  • [ 177976-49-7 ]
  • (2S,1'R)-3-(4-{1'-[(biphenyl-3-ylmethyl)-carbamoy]-ethoxy}-phenyl)-2-ethoxy-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound was prepared from <strong>[177976-49-7]C-<strong>[177976-49-7]biphenyl-3-yl-methylamine</strong></strong> and [(2S,] [L'R)-3- [4- (1'-CARBOXY-ETHOXY)-PHENYL]-2-ETHOXY-PROPIONIC] acid (Example 1, step 2) via the same procedure used for the preparation of [(2S,] [1'R)-2-ETHOXY-3- (4- F 1'- [2- (4-] [PHENOXY-PHENYL)-ETHYLCARBAMOYL]-ETHOXY}-PHENYL)-PROPIONIC] acid (Example 1, step 3) to produce a colorless oil. MS (ES) for [C27H29NO5] [[M+H] +] : [448.] 2.
  • 40
  • [ 847199-08-0 ]
  • [ 177976-49-7 ]
  • [ 864264-18-6 ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate;palladium diacetate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80 - 100℃; for 10 - 16h; Example 90; 7-Chloro-6- (3-phenyl-benzylamino)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine Succinate; Use a method similar to the General Procedure 5-3 to couple 7-chloro-3- (2, 2,2- trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2, 3,4, 5-tetrahydro-1H-benzo [dJazepine (0.3 g, 0.706 mmol) with 3-phenyl-benzylamine (0.388 g, 2.117 mmol) using palladium (II) acetate (32 mg, 0.141 mmol), tris (dibenzylideneacetone) dipalladium (0) (65 mg, 0.070 mmol), BINAP (264 mg, 0.424 mmol) and cesium carbonate (460 rng, 1.412 mmol) in toluene (12 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (1: 0,19 : 1) to give 7-chloro-6- (3-phenyl-benzylamino)-3- (2, 2,2- trifluoroacetyl) -2,3, 4, 5-tetrahydro-lH-benzo [d] azepine as an oil (0.257 g, 79%). MS (ES+) m/z : 459 (M+H) +. Use a method similar to the General Procedure 1-2, using 7-chloro-6- (3-phenyl- benzylamino)-3- (2, 2, 2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (237 mg, 0.516 mmol), to give the free base of the title compound as an oil (188 mg, 100%) that was used without further purification. Use a method similar to the General Procedure 2-1, using 7-chloro-6- (3-phenyl- benzylamino)-2, 3,4, 5-tetrahydro-lH-benzo [dazepine (188 mg, 0.518 mmol) to give the title compound as a white solid (191 mg, 77%). MS (ES+) m/z : 363 (M+H) +. ; General Procedure 5-3; Add the appropriately substituted 3- (2, 2,2-trifluoroacetyl)-6- trifluoromethanesulfonyloxy-2, 3,4, 5-tetrahydro-1H-benzo [d] azepine (1 equiv. ), the appropriate amine (1.2-3. 0 equiv. ), palladium (II) acetate (0.2-0. 4 equiv.), tris (dibenzylideneacetone) dipalladium (0) (0.1-0. 2 equiv. ), BINAP (0.6-1. 2 equiv. ; BINAP/catalysts ratio 2 : 1), cesium carbonate (2-2.5 equiv. ) and toluene or 1,4-dioxane (0. 05-0. 2 M solution) to a flask, degas and fill three times with nitrogen. Heat the mixture at 80-100C for 10-16 h. Dilute the mixture with EtOAc, wash with saturated aqueous NaHCO3 and brine, dry over Na2SO4, filter and concentrate in vacuo to give the crude mixture. Alternatively remove the volatiles from the reaction mixture to give directly the crude mixture, or filter the reaction mixture through Celiez and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc mixtures and further SCX chromatography if needed.
  • 41
  • [ 24973-50-0 ]
  • [ 177976-49-7 ]
YieldReaction ConditionsOperation in experiment
63% Preparation Example 5. C-Biphenyl-3-yl-methylamine To a solution of 3-cyanophenylboronic acid (1.0g, 6.81 mmol) and bromobenzene (1.07g, 6.81mmol) in N,N-dimethylformamide (100mL) were added tetrakis(triphenylphosphine)palladium(0) (0.393g, 0.341 mmol) and cesium carbonate (2.77g, 8.51mmol) under nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and biphenyl-3-carbonitrile (821 mg, 67%) was obtained as a yellow solid. Next, a solution of the resulting biphenyl-3-carbonitrile (821 mg, 4.58mmol) in tetrahydrofuran (5mL) was added to a solution of lithium aluminum hydride (0.435g, 11.5mmol) in tetrahydrofuran (5mL) that had been cooled on an ice bath, and the solution was stirred for 6 hours at room temperature. The reaction solution was cooled on an ice bath, a mixture solution of methanol and water (9:1) was added thereto, an aqueous solution of saturated ammonium chloride was further added, filtration was carried out through Celite pad and insoluble matter was removed. The filtrate was partitioned, the organic layer was dried over anhydrous magnesium sulfate, and the title compound (527mg, 63%) was obtained as a brown oil. This was used in the next reaction without further purification.
63% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 6h; To a solution of 3-cyanophenylboronic acid (1.0g, 6.81 mmol) and bromobenzene (1.07g, 6.81mmol) in N,N-dimethylformamide (100mL) were added tetrakis(triphenylphosphine)palladium(0) (0.393g, 0.341 mmol) and cesium carbonate (2.77g, 8.51mmol) under nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and biphenyl-3-carbonitrile (821 mg, 67%) was obtained as a yellow solid. Next, a solution of the resulting biphenyl-3-carbonitrile (821mg, 4.58mmol) in tetrahydrofuran (5mL) was added to a solution of lithium aluminum hydride (0.435g, 11.5mmol) in tetrahydrofuran (5mL) that had been cooled on an ice bath, and the solution was stirred for 6 hours at room temperature. The reaction solution was cooled on an ice bath, a mixture solution of methanol and water (9:1) was added thereto, an aqueous solution of saturated ammonium chloride was further added, filtration was carried out through Celite pad and insoluble matter was removed. The filtrate was partitioned, the organic layer was dried over anhydrous magnesium sulfate, and the title compound (527mg, 63%) was obtained as a brown oil. This was used in the next reaction without further purification.
  • 42
  • [ 177976-49-7 ]
  • 4-Amino-7-phenyl-1,2,3,4-tetrahydroisoquinolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step C Following General Procedure 5-D and using 3-(phenyl)benzyl amine, the title compound was prepared.
Step C: Following General Procedure 5-D and using 3-(phenyl)benzyl amine, the title compound was prepared.
  • 43
  • NaCNBH4 [ No CAS ]
  • NH3/MeOH [ No CAS ]
  • [ 1204-60-0 ]
  • [ 177976-49-7 ]
YieldReaction ConditionsOperation in experiment
In methanol; Step B To a solution of 3-biphenylcarboxaldehyde (0.011 eq.) in 30 mL of methanol was added 10 eq. of 7N NH3/MeOH and NaCNBH4 (2 eq.). A yellow gum precipitated from solution. The solution was then heated at 60 C. until gum dissolved and the solution was stirred at room temperature overnight. The reaction mixture was then concentrated and the resulting residue diluted with ice water and ethyl acetate. The organic layer was then washed with brine and extracted with 5N HCl. The pH of the aqueous layer was then adjusted to 12 and the aqueous layer was extracted with cold ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to give 3-(phenyl)benzyl amine as an oil.
In methanol; Step B: To a solution of 3-biphenylcarboxaldehyde (0.011 eq.) in 30 mL of methanol was added 10 eq. of 7N NH3/MeOH and NaCNBH4 (2 eq.). A yellow gum precipitated from solution. The solution was then heated at 60 C. until gum dissolved and the solution was stirred at room temperature overnight. The reaction mixture was then concentrated and the resulting residue diluted with ice water and ethyl acetate. The organic layer was then washed with brine and extracted with 5N HCl. The pH of the aqueous layer was then adjusted to 12 and the aqueous layer was extracted with cold ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to give 3-(phenyl)benzyl amine as an oil.
  • 44
  • [ 39959-54-1 ]
  • [ 98-80-6 ]
  • [ 177976-49-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In ethanol; toluene; REFERENCE EXAMPLE 3 Preparation of 3-phenylbenzylamine 18.25 g of 3-bromobenzylamine hydrochloride, 17.39 g of sodium carbonate in aqueous solution (120 ml) and 1.90 g of tetrakis(triphenylphosphine)palladium (0) were added to toluene (240 ml) under a nitrogen atmosphere. The resulting solution was mixed with 10.00 g of phenylboric acid in ethanol (120 ml) at room temperature with stirring and refluxed under heating for 2 hours. After the reaction, the reaction solution was cooled to room temperature, poured into saturated aqueous sodium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent to give 11.18 g of crude 3-phenylbenzylamine as a brown viscous liquid.
  • 45
  • [ 177976-49-7 ]
  • [ 79-22-1 ]
  • [ 220512-13-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In toluene; PREPARATION EXAMPLE 1 Preparation of Methyl N-(3-phenylbenzyl)carbamate (Compound No. 1-1) 11.18 g of <strong>[177976-49-7]3-phenylbenzylamine</strong> in toluene (250 ml) was mixed with 7.24 g of pyridine at room temperature. The resulting solution was stirred under cooling with ice while 9.58 g of methyl chloroformate was added dropwise and then stirred at room temperature for 2 hours. After the reaction, the reaction solution was poured into aqueous citric acid and extracted with ethyl acetate, and the organic layer was washed with aqueous citric acid, dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 8.61 g of methyl N-(3-phenylbenzyl)carbamate as pale yellow crystals. m.p. 49-52 C. 1H-NMR: (CDCl3/TMS, delta (ppm)) 3.70 (s, 3H), 4.43 (d, 2H), 5.06 (br, 1H), 7.16-7.59 (m, 9H).
  • 46
  • [ 317364-83-3 ]
  • [ 177976-49-7 ]
  • [ 317823-99-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 33 2-[3-Phenylbenzylamino]-4-[benzimidazol-1-yl]pyrimidine 2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine was reacted with <strong>[177976-49-7]3-phenylbenzylamine</strong> according to the procedure described in EXAMPLE 1, Step C to afford the title compound. Mass Spectrum (ESI): m/e 378.1 (M+1). 1H NMR (500 MHz, CDCl3): delta 8.60 (s, 1H); 8.44 (br s, 1H); 8.09 (br s, 1H); 7.85 (m, 1H); 7.65 (s, 1H); 7.59 (d, J=7.3 Hz, 2H); 7.56 (m, 1H); 7.41-7.49 (m, 4H); 7.36 (m, 3H); 6.85 (d, J=5.2 Hz, 1H); 5.83 (br s, 1H); 4.83 (d, J=5.9 Hz, 2H).
  • 47
  • [ 273726-95-7 ]
  • [ 177976-49-7 ]
  • [ 273726-96-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; In dichloromethane; EXAMPLE 77 4'-Trifluoromethyl-biphenyl-2-carboxylic Acid [4-(4[(biphenyl-3-ylmethyl)-carbamoyl]-methyl}piperazin-1-yl)-phenyl]-amide To a stirred solution of (4-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-phenyl}-piperazin-1-yl)-acetic acid (241 mg), <strong>[177976-49-7]biphenyl-3-yl-methylamine</strong> (95 mg), HOBt (87 mg), and Et3N (202 mg) in CH2Cl2 (20 mL) was added EDCl (125 mg) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography eluding with CH2Cl2/MeOH (97/3) and the solid obtained was recrystallized from EtOH to give the title compound (180 mg) as white crystals. m.p.: 165-167 C. Analysis for C39H35F3N4O2 Calculated: C,72.21; H,5.44; N,8.64; Found: C,71.94; H,5.66; N,8.53%.
With NaHCO3; benzotriazol-1-ol; triethylamine; In dichloromethane; EXAMPLE 77 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(4-[(biphenyl-3-ylmethyl)-carbamoyl]-methyl}-piperazin-1-yl)-phenyl]-amide To a stirred solution of (4-{4-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-phenyl}-piperazin-1-yl)-acetic acid (241 mg), <strong>[177976-49-7]biphenyl-3-yl-methylamine</strong> (95 mg), HOBt (87 mg), and Et3N (202 mg) in CH2Cl2 (20 mL) was added EDCl (125 mg) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography eluding with CH2Cl2/MeOH (97/3) and the solid obtained was recrystallized from EtOH to give the title compound (180 mg) as white crystals. m.p: 165-167 C.
  • 48
  • [ 177976-49-7 ]
  • N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-3-phenylbenzylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
11.9% Synthesis Example 6 3-Phenylbenzylamine (3.93 g) was processed in a similar manner as in Synthesis Example 5, whereby trans-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-<strong>[177976-49-7]3-phenylbenzylamine</strong> (Compound 7) and cis-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-<strong>[177976-49-7]3-phenylbenzylamine</strong> (Compound 8) were obtained in amounts of 2.73 g (yield: 45%) and 0.72 g (yield: 11.9%), respectively. The followings are their NMR spectrum data: 1 H-NMR (CDCl3,delta ppm) of Compound 7: 1.24(9H,s), 2.22(3H,s), 3.08(2H,dd), 3.55(3H,s), 5.66(1H,dt), 6.11(1H,dt), 7.25-7.68(9H,m). 1 H-NMR (CDCl3,delta ppm) of Compound 8: 1.24(9H,s), 2.26(3H,s), 3.31(2H,dd), 3.59(3H,s), 5.63(1H,dt), 5.97(1H,dt), 7.26-7.67(9H,m).
  • 49
  • [ 911705-07-2 ]
  • [ 177976-49-7 ]
  • [ 911705-06-1 ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20℃; for 1 - 3h; General procedure D: (Amide-Formation)To a stirred solution of 1.0 mmol of "acid" and "1.0 mmol of "amin" in 20 ml of dichloromethane are added 5.0 mmol of triethylamin and 1.0 mmol of tri-propylphosphonic acid cyclic anhydride [68957-94-8] (50% in ethyl acetate) at room temperature. The reaction mixture is stirred for 1-3 hours, diluted with dichloromethane, washed with 1 N hydrochloric acid and brine. The organic phases are combined, dried over sodium sulfate and the solvent is concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound.; According to general procedure D, 0.07 g of (2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3- methoxy-propyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-ylmethoxy]piperidine-1 ,2-dicarboxylic acid 1 -benzyl ester and <strong>[177976-49-7]3-phenylbenzylamine</strong> are reacted to afford the title compound as a colourless solid. Rf = 0.15 (EtOAc-heptan 1 :1); Rt = 5.62.
  • 50
  • [ 177976-49-7 ]
  • methyl 4-([(1,1'-biphenyl-3-ylmethyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 310 methyl 4-([(1,1'-biphenyl-3-ylmethyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate The title compound was prepared using the procedure described in Example 309E except using 1,1'-biphenyl-3-ylmethylamine instead of 1-naphthylmethylamine. 1H NMR (DMSO-D6) delta 4.02 (S, 3H); 4.43 (D, 2H); 6.89 (m, 1H); 7.36 (m, 2H); 7.42-7.51 (m, 4H); 7.56 (m, 1H), 7.60-7.72 (m, 4H); 7.82 (m, 1H); 8.42 (S, 1H); 9.04 (S, 1H).
EXAMPLE 310 methyl 4-([(1,1'-biphenyl-3-ylmethyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate The title compound was prepared using the procedure described in Example 309E except using 1,1'-biphenyl-3-ylmethylamine instead of 1-naphthylmethylamine. 1H NMR (DMSO-D6) delta 4.02 (S, 3H); 4.43 (D, 2H); 6.89 (M, 1H); 7.36 (M, 2H); 7.42-7.51 (M, 4H); 7.56 (M, 1H), 7.60-7.72 (M, 4H); 7.82 (M, 1H); 8.42 (S, 1H); 9.04 (S, 1H).
  • 51
  • [ 1028338-59-1 ]
  • [ 177976-49-7 ]
  • [ 1028337-29-2 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ISOPROPYLAMIDE; at 80℃; for 1.5h; Example 125: Synthesis of 6-[(Biphenyl-3-ylmethyl)-amino]-4-chloro-2H- phthalazin-1-one; A mixture 6-bromo-4-chloro-2H-phthalazin-l-one (95mg, 0.366 mmol), 3- phenylbenzylamine (95mg, 0.518 mmol), Pd2(dba)3 (40mg, 0.044 mmol), rac-BINAP(76mg, 0.122 mmol) and NaO'Bu (lOlmg, 1.05 mmol) in DMA (5mL) was heated at8O0C for 1.5h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4).Chromatography on silica (EtOAc/hexanes) afforded 6-[(biphenyl-3-ylmethyl)-amino]-4- chloro-2H-phthalazin-l-one (3 mg) as an off white solid, 1H (400 MHz, CDCl3) delta: 4.49(s, 2H), 7.00 (m, 2H), 7.50 (m, 9H), 8.05 (d, IH), 10.87 (s, IH) ppm; m/z (M+l) 361.95.
  • 52
  • [ 911702-67-5 ]
  • [ 177976-49-7 ]
  • [ 911705-06-1 ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 1 - 3h; To a stirred solution of 1.0 mmol of "acid" and "1.0 mmol of "amin" in 20 ml of dichloromethane are added 5.0 mmol of triethylamin and 1.0 mmol of tri-propylphosphonic acid cyclic anhydride [68957-94-8] (50% in ethyl acetate) at room temperature. The reaction mixture is stirred for 1-3 hours, diluted with dichloromethane, washed with 1 N hydrochloric acid and brine. The organic phases are combined, dried over sodium sulfate and the solvent is concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound.
  • 53
  • [ 141-30-0 ]
  • [ 177976-49-7 ]
  • [ 1145786-46-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 131℃; for 2h;microwave irradiation; 3,6-Dichloropyridazine (200 mg), (3-biphenylylmethyl)amine (244 mg), K2CO3 (184 mg) and NMP (1.33 ml) were sonicated for 1 hour then heated at 131 0C for 2 hours in a microwave reactor. The reaction mixture was partitioned between H2O (100 ml) and EtOAc (100 ml) and the aqueous solution extracted with EtOAc (2 x 100 ml). The organic solutions were combined, dried over MgSO4, filtered and evaporated to give the crude product. This was purified by flash column chromatography on silica, eluting with <n="22"/>a 0-50 % mixture of EtOAc in hexane which gave the title compound (117 mg) as a yellow solid.deltaH (CDCI3, 400MHz): 4.67 (2H, d), 5.2 (1 H, br s), 6.64 (1 H, d), 7.16 (1 H, d), 7.30-7.40 ((22HH,, mm)),, 77..4400--77..5500 (3H, m), 7.50-7.67 (4H, m). MS (ES): C17H1435CIN3 requires 295; found 294 [M+H]+.
  • 54
  • [ 177976-49-7 ]
  • [ 203436-45-7 ]
  • [ 1056016-62-6 ]
  • 55
  • [ 177976-49-7 ]
  • [ 616-79-5 ]
  • C20H17N3O3 [ No CAS ]
  • 56
  • [ 933-20-0 ]
  • [ 177976-49-7 ]
  • [ 1189819-48-4 ]
  • 57
  • [ 5345-47-1 ]
  • [ 177976-49-7 ]
  • [ 1185088-41-8 ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 4h; Production example 5 0.88 g of a BOP reagent and 0.40 g of triethylamine were successively added to a mixture of 0.28 g of 2-aminonicotinic acid, 0.37 g of <strong>[177976-49-7]3-phenylbenzylamine</strong> and 10 ml of DMF. The obtained mixture was stirred at a room temperature for 4 hours. Thereafter, ice and a saline solution were successively added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was further washed with a saline solution 3 times, and it was then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. 0.77 g of the obtained residue was subjected to silica gel column chromatography, so as to obtain 0.58 g of N-(3-phenylphenyl)methyl-2-aminonicotinic acid amide (hereinafter referred to as the present compound 5).The present compound 5 [Show Image] [Show Image] 1H-NMR (DMSO-D6) delta: 4.52 (2H, d, J = 5.8 Hz), 6.60 (1H, dd, J = 7.8, 4.9 Hz), 7.07 (2H, br), 7.31-7.49 (5H, m), 7.53-7.55 (1H, m), 7.61-7.65 (3H, m), 7.97 (1H, dd, J = 7.8, 2.0 Hz), 8.07-8.09 (1H, m), 9.01-9.04 (1H, m).
  • 58
  • [ 177976-49-7 ]
  • [ 96989-50-3 ]
  • [ 2381-75-1 ]
  • 5-(4-chlorobenzyloxymethyl)-4-(3-phenylbenzyl)-2,4-dihydro[1,2,4]triazole-3-thiol potassium salt [ No CAS ]
  • 59
  • [ 177976-49-7 ]
  • [ 100-52-7 ]
  • [ 1283596-05-3 ]
  • 60
  • [ 177976-49-7 ]
  • [ 100-52-7 ]
  • [ 1048118-05-3 ]
YieldReaction ConditionsOperation in experiment
Typical procedure: To a stirred solution of the amine (1.0 equiv) and the aldehyde (1.0 equiv) in dichloroethane (0.2 M) was added acetic acid (5.0 equiv). The solution was stirred for 18 h, then sodium triacetoxyborohydride (1.2 equiv) was added and the mixture was stirred for 1 h. The appropriate isocyanate (1.5 equiv) was added and the mixture was stirred for an additional 4 h before being quenched with a saturated aqueous solution of sodium bicarbonate. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic layers were combined and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel.
  • 61
  • [ 177976-49-7 ]
  • [ 126542-95-8 ]
  • [ 1357026-39-1 ]
  • 62
  • [ 1347758-05-7 ]
  • [ 177976-49-7 ]
  • [ 1347756-70-0 ]
  • 63
  • [ 37527-66-5 ]
  • [ 177976-49-7 ]
  • [ 1362623-71-9 ]
  • 64
  • [ 1312608-17-5 ]
  • [ 177976-49-7 ]
  • [ 1312607-85-4 ]
  • 65
  • [ 108-77-0 ]
  • [ 177976-49-7 ]
  • C16H12Cl2N4 [ No CAS ]
  • 66
  • [ 177976-49-7 ]
  • C28H26ClF3N6O2S [ No CAS ]
  • 67
  • [ 177976-49-7 ]
  • [ 1394122-41-8 ]
  • 68
  • [ 937026-26-1 ]
  • [ 177976-49-7 ]
  • [ 1304134-79-9 ]
  • 74
  • [ 177976-49-7 ]
  • 2-amino-6-(trans-2-phenylcyclopropane-1-amino)-N-(3-phenylbenzyl)hexanamide dihydrochloride [ No CAS ]
  • 76
  • [ 177976-49-7 ]
  • [ 96989-50-3 ]
  • 1-(isothiocyanatomethyl)-3-phenylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 55℃; for 1.5h;Molecular sieve; To a solution of 0.25 M di-pyridyl-thiocarbonate in DMF (stored on molecular sieves 3A) (1.05 eq) was added 0.1 M amine (free base) 0.1 M in DMF (1eq). The reaction mixture was heated at 55 C for 1.5 h.
  • 77
  • [ 177976-49-7 ]
  • 1-(4-chlorophenoxyacetyl)-4-(3-phenylbenzyl)-thiosemicarbazide [ No CAS ]
  • 78
  • [ 177976-49-7 ]
  • tert-butyl ((4-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)carbamate [ No CAS ]
  • 79
  • [ 177976-49-7 ]
  • Umemoto's reagent [ No CAS ]
  • C14H12F3N [ No CAS ]
  • 80
  • [ 1384546-18-2 ]
  • [ 177976-49-7 ]
  • [ 68498-54-4 ]
  • [ 1384544-71-1 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 50℃; The corresponding aldehyde-acid of the general formula B1 (1.0 eq.) and primary biaryl amine (1.0 eq.) were dissolved in MeOH and stirred at 20 C. for 10 min. Then suitable isonitrile (1.2 eq.) was added and the resultant mixture was heated at 50 C. for 1-5 hs at stirring. After the reaction was completed the reaction mixture was cooled till 20 C., the solid precipitated was filtered of and washed with methanol. The prepared compound was recrystallized from ester or purified by chromatograpy on SiO2 using as eluent CH2Cl2 with appropriate methanol gradient. Structures of compounds were confirmed by LCMS data. [0211] Using this procedure compounds 81-87, 89-101 were prepared: [0212] 81: Molecular weight (M.w.) 508.55, LCMS m/z 509 (M+1);
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