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CAS No. : | 205688-13-7 | MDL No. : | MFCD12912141 |
Formula : | C21H18N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ALQJHOXOLDYSLS-UHFFFAOYSA-N |
M.W : | 330.38 | Pubchem ID : | 11450338 |
Synonyms : |
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 99.41 |
TPSA : | 64.35 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.52 cm/s |
Log Po/w (iLOGP) : | 2.55 |
Log Po/w (XLOGP3) : | 3.94 |
Log Po/w (WLOGP) : | 4.45 |
Log Po/w (MLOGP) : | 3.41 |
Log Po/w (SILICOS-IT) : | 3.38 |
Consensus Log Po/w : | 3.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.57 |
Solubility : | 0.00882 mg/ml ; 0.0000267 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.99 |
Solubility : | 0.00337 mg/ml ; 0.0000102 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.23 |
Solubility : | 0.0000194 mg/ml ; 0.0000000586 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.41 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
90% | Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
V.4 (4) (4) HF Cleavage The resin bearing the desired amino acid sequence (1.0 gram) is placed in a Teflon reaction vessel, and anhydrous anisole (1 mL) is added. The vessel is cooled with liquid N2, and anhydrous HF (10 mL) is distilled into it. The temperature is raised with iced water to 0° C. The mixture is stirred at this temperature for 1 hour, and then the HF is distilled off at 0° C. The residue is washed with anhydrous ether, and the peptide is extracted with a 1:1 mixture of CH3CN:H2O. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile at 20℃; | 13.d λ/jλ/'-Disuccinimidylcarbonate (16.20 g, 63.26 mmol, 1.1 eq) is added at room temperature to a stirred solution of N-(4-aminophenyl)(fluoren-9- ylmethoxy)carboxamide (20.00 g, 60.53 mmol, 1.0 eq) in CH3CN (1100 ml_). After stirring overnight at room temperature, the reaction mixture is filtered to afford 28.50 g of the expected crude product as a white powder.1 H-NMR (DMSO-CZ6): 2.83 (br, 4H); 4.31 (t, J = 6.4, 1 H); 4.48 (m, 2H); 7.20-7.50 (m, 8H); 7.5 (d, J = 7.4, 2H); 7.91 (d, J = 7.4, 2H); 9.72 (br, 1 H); 10.67 (br, 1 H). | |
In acetonitrile at 20℃; | 43 iV,JV'-Disuccinimidylcarbonate (16.20 g, 63.26 mmol, 1.1 eq) was added at room temperature to a stirred solution of N- (4- aminophenyl) (fluoren-9-ylmethoxy) carboxamide (20.00 g, 60.53 mmol, 1.0 eq) in CH3CN (1100 mL) . After stirring overnight at room temperature, the reaction mixture was filtered to afford 28.50 g of the expected crude product as a white powder. IH-NMR (DMSO-de) : 2.83 (br, 4H); 4.31 (t, J = 6.4, IH); 4.48 (m, 2H); 7.20-7.50 (m, 8H); 7.5 (d, J = 7.4, 2H); 7.91 (d, J = 7.4, 2H); 9.72 (br, IH) ; 10.67 (br, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; | 13.c TFA (55.30 ml_, 717.76 mmol, 15.0 eq) is added at 0 0C to a stirred solution of (fe/t-butoxy)-N-{4-[(fluoren-9-ylmethoxy)carbonylamino]phenyl}carboxamide (20.60 g, 47.85 mmol, 1.0 eq) in CH2CI2 (900 ml_). The resulting solution is allowed to warm to room temperature. After stirring overnight at room temperature, the reaction mixture is concentrated to dryness and the residue is triturated in water. Then the mixture is filtered to afford 15.80 g of the expected crude product as a white powder. 1 H-NMR (DMSO-CZ6): 4.30 (t, J = 6.4, 1 H); 4.49 (d, J = 6.4, 2H); 7.06 (d, J = 7.7, 2H); 7.40 (m, 6H); 7.74 (d, J = 7.4, 2H); 7.91 (d, J = 7.4, 2H); 8.95 (br, 2H); 9.73(br, 1 H). | |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; | 43 TFA (55.30 mL, 717.76 mmol, 15.0 eq) was added at 0 0C to a stirred solution of ( tert-butoxy) -N- {4- [ (fluoren-9-yl- methoxy) carbonylamino] phenyl }carboxamide_(20.60 g, 47.85 mmol, 1.0 eq) in CH2CI2 (900 mL) . The resulting solution was allowed to come at room temperature. After stirring overnight at room temperature, the reaction mixture was concentrated to dryness and the residue was triturated in water. Then the mixture was filtered to afford 15.80 g of the expected crude product as a white powder.IH-NMR (DMSO-d6) : 4.30 (t, J = 6.4, IH); 4.49 (d,- J =6.4, 2H); 7.06 (d, J= 7.7, 2H); 7.40 (m, 6H); 7.74 (d, J= 7.4, 2H); 7.91 (d, J= 7.4, 2H); 8.95 (br, 2H); 9.73 (br, IH) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; solid phase reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; solid phase reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In tetrahydrofuran at 0 - 20℃; for 18.2h; | 9 6.5.9 4-((4-Aminophenyl)carbamoyl)-1H-imidazole-5-carboxylic acid (7) General procedure: The title compound was synthesized from 17 (100 mg, 0.233 mmol) and (9H-fluoren-9-yl)methyl (4-aminophenyl)carbamate (153.8 mg, 0.466 mmol) as described above in the method B. Pale yellow solid, yield 72%; 1H NMR (300MHz, DMSO-d6) δ 8.362 (s, 1H), 8.267(d, J=9.1, 1H), 7.804 (m, 2H), 7.106 (dd, J=5.4, 6.0, 1H); 13C NMR (100MHz, DMSO-d6) δ 161.22, 159.91, 137.68, 136.25, 133.12, 129.23, 127.93, 123.25, 122.44; ESI-MS: 247 [M+1]+; HRESI-MS: m/z calcd for C11H11N4O3 ([M+H]+) 247.0831; found 247.0815. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: C23H36N4O11 With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane for 0.5h; Inert atmosphere; Stage #2: (9H-fluoren-9-yl)methyl (4-aminophenyl)carbamate With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 5 Sodium hydroxide (51 mg, 1.8 mmol, 5 eq.) was added to a solution of compound 2 (0.2 g, 0.36 mmol) in a 4/1 methanol/water mixture (5 ml). The reaction mixture was stirred for 2 h at 85° C. and stopped. The mixture was evaporated to dryness and 30 ml of dichloromethane was added. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product in the form of acid was obtained in the form of an orange foam and was used without further purification. The coupling reagent BOP (0.13 g, 0.29 mmol, 1.3 eq. per acid) was added under argon to a solution of carboxylic acid derivative (0.12 g, 0.23 mmol, 1.0 eq) in 5 mL of distilled dichloromethane. After 30 min, aniline derivative 3 (WO 2009037229) (76 mg, 0.25 mmol, 1.1 eq.) diluted in 0.5 ml of N,N′-dimethylformamide and N,N-diisopropylethylamine (90 pi, 0.5 mmol, 2 eq. per amine) was added. The reaction mixture was stirred overnight at room temperature. 40 ml of dichloromethane was added and the organic phase was washed with 1N hydrochloric acid solution (2×20 ml), brine (2×20 ml) and water (1×20 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral alumina gel (dichloromethane/methanol 99.5-0.5 to 99/1) to give 4 in the form of a pale yellow oil in 62% yield. Compound 4 may be used as a synthon to form a radiolabelable moiety or group R according to the invention. (0355) 1H NMR (300 MHz, DMSO-d6) δ 1.33 (s, 9H, NHCOOC(CH3)3), 1.52 (m, J=6.6 Hz, 2H, CH2CH2CH2NHCOO), 1.84 (m, J=6.0 Hz, 2H, ArH-NHCH2CH1CH2), 2.91 (q, J=6.6 Hz, 2H, CH2CH2CH2NHCOO), 3.03 (q, J=6.0 Hz, 2H, ArH-NHCH2CH2CH2), 3.40 to 3.55 (m, 12H, OCH2CH2O and OCH2CH2CH2), 4.28 (t, J=6.6 Hz, 2H, CH2CH), 4.47 (d, J=6.6 Hz, 2H, CH2CH), 6.71 (t, J=5.2 Hz, 1H, NHCOOC(CH3)3), 7.30 to 7.50 (m, 6H, ArFmocH and Ar2H), 7.62 (d, J=8.6 Hz, 2H, Ar2H), 7.73 (d, J=7.4 Hz, 2H, ArFmocH), 7.91 (d, J=7.4 Hz, 2H, ArFmocH), 8.72 (t, J=4.8 Hz, 1H, ArH-NHCH2), 8.88 (s, 2H, Ar1H), 9.71 (s, 1H, Ar2H-NHCOO), 8.72 (t, J=4.8 Hz, 1H, Ar2H-NH-Ar1H); 13C NMR (75 MHz, DMSO-d6) δ 30.1, 30.8, 31.7, 39.1, 47.4, 48.5, 67.4, 69.8, 70.8, 71.4, 71.45, 71.5, 71.55, 79.1, 120.4, 121.2, 121.9, 122.9, 127.0, 128.9, 129.5, 133.0, 135.2, 136.9, 138.7, 142.7, 145.7, 155.2, 157.3, 163.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44 % de | Stage #1: (9H-fluoren-9-yl)methyl (4-aminophenyl)carbamate; C14H18N3O3PolS2 In dimethyl sulfoxide for 0.0833333h; Stage #2: hydroxy-2-propanone With <i>L</i>-proline In dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere; Sealed tube; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.634 g | In dichloromethane for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With HATU |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile at 20℃; | Synthesis of Fmoc-Diamine (10) To a solution of 1, 4-phenylenediamine (1 mmol, 0.1 g) in ACN (5 ml), fmoc-OSu (1 mmol, 0.33 g) was added dropwise. The mixture was stirred at room temperature for 1 h. The progress of the reaction was monitored using TLC. After completion the reaction, the resultant precipitate was filtered and washed with ACN. White powder; Yield: > 90%; M.P. 201 °C; IR (KBr, cm-1): 3391, 3311, 3204, 3042, 2947, 1688. 1H-NMR (500 MHz, DMSO-d6): 4.29 (t, j = 6.5 Hz, 1H, CH), 4.41 (d, j = 6.2, 2H, CH2), 5.1 (brs, 2H, NH2), 6.53 (d, j = 6.2 Hz, 2H, Ar-H), 7.1 (d, j = 6.2 Hz, 2H, Ar-H), 7.36 (t, j = 7.0 Hz, 2H, Ar-H), 7.44 (t, j = 7.2 Hz, 2H, Ar-H), 7.76 (d, j = 7.0, 2H, Ar-H), 7.92 (d, j = 7.4 Hz, 2H, Ar-H), 9.6 (s, 1H, NH). 13C NMR (125 MHz, DMSO-d6): 46.7, 65.3, 114.4, 120.2, 120.3, 125.2, 127.1, 127.7, 140.8, 143.9, 154.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran; dichloromethane Reflux; | Synthesis of Protected UAA2: (11a) The mixture of Fmoc-protected diamine (1 mmol, 0.31 g) and Meldrum’s acid (1 mmol, 0.1 g) were refluxed overnight in THF/DCM (1:1 mL). The mixture was concentrated and the residual was washed with ethyl acetate and filtered to give pure product. White powder, Yield: > 80%; M.P. 231 °C IR (KBr, cm-1): 3326, 2970, 1729, 1699, 1665 1H-NMR (500 MHz, DMSO-d6): 3.32 (s, 2H, CH2), 4.30 (t, j = 6.5 Hz, 1H, CH), 4.46 (d, j = 6.2 Hz, 2H, CH2), 7.33-7.47 (m, 8H, Ar-H), 7.75 (d, j = 7.2 Hz, 2H, Ar-H), 7.90 (d, j = 7.6 Hz, 2H, Ar-H), 9.64 (s, 1H, NH), 10.03 (s, 1H, NH). 13CNMR (125 MHz, DMSOd6): 43.8, 46.6, 65.5, 118.7, 119.6, 120.2, 125.1, 127.1, 127.7, 133.8, 140.8, 143.8, 153.4, 164.2, 169.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetone at 20℃; | Synthesis of Protected UAA3: (11b) Fmoc-protected diamine (1 mmol, 0.31 g) and succinic anhydride (1 mmol, 0.11 g) were dissolved in dry Acetone (5 mL). The mixture was stirred overnight. After completion of the reaction (checked by TLC), the mixture was filtered and washed with ethyl acetate to give pure product. White powder. Yield: > 80%; M.P. 240 °C. IR (KBr, cm-1): 3312, 3054, 2936, 1700, 1663, 1H-NMR (500 MHz, DMSO-d6): 2.49-2.52 (m, 4H, CH2), 4.29 (t, j = 6.5 Hz, 1H, CH), 4.46 (d, j = 6.0 Hz, 2H, CH2), 7.31-7.49 (m, 10H, Ar-H), 7.73 (d, j = 7.2, 2H, Ar-H), 7.88 (d, j = 7.35, 2H, Ar-H), 9.60(s, 1H, NH), 9.86 (S, 1H, NH), 11.9 (brs, 1H, COOH). 13CNMR (125 MHz, DMSO-d6): 28.9, 30.9, 46.7, 65.5, 118.7, 119.4, 120.2, 125.1, 127.1, 127.7, 134.1, 134.3, 140.8, 143.9, 153.5, 169.7, 173.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetone at 20℃; | Synthesis of Protected UAA3: (11b) General procedure: Fmoc-protected diamine (1 mmol, 0.31 g) and succinic anhydride (1 mmol, 0.11 g) were dissolved in dry Acetone (5 mL). The mixture was stirred overnight. After completion of the reaction (checked by TLC), the mixture was filtered and washed with ethyl acetate to give pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (9H-fluoren-9-yl)methyl (4-aminophenyl)carbamate With 2,4,6-trimethyl-pyridine In N,N-dimethyl-formamide for 16h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Stage #3: Nα-Fmoc-(4-benzyloxy)-L-phenylglycine; trifluoroacetic acid; hexanoic acid Further stages; |
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