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CAS No. : | 116668-47-4 | MDL No. : | MFCD01861831 |
Formula : | C11H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NZTPZUIIYNYZKT-UHFFFAOYSA-N |
M.W : | 187.19 | Pubchem ID : | 2733954 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 55.31 |
TPSA : | 63.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.6 cm/s |
Log Po/w (iLOGP) : | 1.26 |
Log Po/w (XLOGP3) : | 2.6 |
Log Po/w (WLOGP) : | 2.13 |
Log Po/w (MLOGP) : | 2.02 |
Log Po/w (SILICOS-IT) : | 1.61 |
Consensus Log Po/w : | 1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.148 mg/ml ; 0.000792 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.58 |
Solubility : | 0.0494 mg/ml ; 0.000264 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.09 |
Solubility : | 0.153 mg/ml ; 0.000815 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; NaOH; In water; tert-butyl alcohol; | Example 4.1Synthesis of 6-(tert-butoxycarbonylamino)-2-naphthoic acid (7)Boc2O (280 mg, 1.28 mmol) and NaOH (40 mg, 1.0 mmol) were added to a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (200 mg, 1.07 mmol) in t-BuOH (6 mL) and H2O (6 mL).The reaction mixture was stirred at room temperature for 12 hours, after which it was diluted with water and washed with CH2Cl2.The aqueous layer was adjusted to a pH level of about 2 with 2N HCl and extracted with ethyl acetate.The organic layer was dried over Na2SO4, and the filtrate was concentrated and purified by silica column chromatography (ethyl acetate/hexane=1/1) (300 mg, 98percent).1H-NMR (CD3OD) 8.48 (s, 1H), 8.05 (s, 1H), 7.95 (d, J=8.4, 1H), 7.86 (d, J=8.7, 1H), 7.75 (d, J=8.7, 1H), 7.51 (d, J=8.8, 1H) 1.53 (s, 9H) ppm; ESI-MS m/z calcd for C16H17N2O: 287.3105. found 288.8273 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With potassium carbonate; sodium iodide; In DMF (N,N-dimethyl-formamide); at 80℃; | To a solution (40 [ML)] of 6-amino-2-naphtoic acid [(0.] [500G,] 2.67 mmol) in DMF were added benzyl bromide (1.142 g, 6.68 [MMOL),] potassium carbonate (1. [107 G,] 8.01 mmol) and sodium iodide (1.201 g, 8.01 mmol), and the mixture was stirred at [80°C] overnight. After cooled to room temperature, the mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The separated organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane: ethyl acetate, 3: 1) to give benzyl 6- [(BENZYLAMINO)-2-NAPHTHOATE] (0.214 g, [21percent)] as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Reference Example 99; ethyl 6-amino-2-naphthoate; [Show Image] 6-Amino-2-naphthoic acid (10.50 g) was suspended in ethanol, thionyl chloride (8.0 mL) was added dropwise thereto, and the mixture was heated under reflux overnight. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in THF, and the solution was diluted with ethyl acetate, and filtered through NH silica gel (50 g). The filtrate was concentrated under reduced pressure. The residue was crystallized from water, and the crystals were collected by filtration, washed with water, and dried under reduced pressure to give the title compound (16.50 g, yield 70percent) as a brown solid. 1H NMR (300 MHz, CDCl3) delta: 0.31 - 0.46 (m, 2 H) 0.60 - 0.75 (m, 2 H) 1.21 - 1.39 (m, 1 H) 1.45 (t, J=7.06 Hz, 3 H) 3.88 (d, J=6.97 Hz, 2 H) 4.44 (q, J=7.10 Hz, 2 H) 7.00 (d, J=8.85 Hz, 2 H) 7.63 (dd, J=8.85, 2.07 Hz, 1 H) 7.79 - 8.01 (m, 5 H) 8.06 (dd, J=8.48, 1.70 Hz, 1 H) 8.40 (d, J=2.07 Hz, 1 H) 8.56 (s, 1 H). | |
With thionyl chloride; for 3h;Heating / reflux; | Z. 1-Chloro-6-fluoro-2-aminonaphthalene To a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (1 g, 5.34 MMOL) in ethanol (20 mL), is added dropwise thionyl chloride (0.622 mL, 10.7 MMOL). The resulting reaction solution is heated to reflux temperature under a N2 atmosphere for 3 hours. Concentration and trituration with methanol gives <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> ethyl ester as a brown oil. A mixture of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> ethyl ester (500 mg, 2.32 MMOL) and nitrosonium tetrafluoroborate (298 mg, 2.56 MMOL) in 1, 2-dichlorobenzene (10 mL) is stirred at room temperature for 12 hours and at 110°C for 1 hour. After cooling to room temperature, the reaction mixture is concentrated by rotary evaporator under high vacuum. The residual oil is purified by flash chromatography on silica gel (DICHLOROMETHANE) to give 6-fluoro-2-naphthoic acid ethyl ester as a yellow oil. To a solution of 6-fluoro-2-naphthoic acid ethyl ester (600 mg, 2.75 MMOL) in ethanol (10 mL) at room temperature, is added 1 N NAOH (2.75 mL, 2.75 MMOL). After stirring at room temperature for 4 hours, water (10 mL) is added. Acidification (2 N HCI) and filtration gives 6-fluoro-2-naphthoic acid as a white solid. To a suspension of 6-fluoro-2-naphthoic acid (450 mg, 2.37 MMOL) and triethylamine (0.66 mL, 4.73 MMOL) in 1,4-dioxane (30 mL) at room temperature, is added DPPA (0.77 mL, 3.55 MMOL). After stirring at room temperature for 2.5 hours, ethanol (1.38 mL, 23.7 MMOL) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (NA2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3: 1 hexanes/EtOAc) GIVES N- (6-FLUORO-2- naphthyl) carbamic acid ethyl ester as an oil. A mixture of N-(6-fluoro-2-naphthyl) carbamic acid ethyl ester (548 mg, 2.35 MMOL), N-CHLOROSUCCINIMIDE (313 mg, 2.35 MMOL) and 1 M HCI in acetic acid (2.35 mL, 2.35 MMOL) in acetic acid (20 mL) is heated at 50°C under N2 atmosphere for 1 hour. After cooling to room temperature, water (10 mL) is added. The resulting precipitate is removed by filtration to GIVE LS (1-CHLORo-6-FLUORO-2-NAPHTHYL) CARBAMIC acid ethyl ester as a yellow solid. A mixture OF N-(1-CHLORO-6-FLUORO-2-NAPHTHYL) carbamic acid ethyl ester (600 mg, 2.24 MMOL) and KOH (1.51 g, 26.9 MMOL) in ethanol (20 mL) is heated to reflux temperature under N2 atmosphere for 12 hours. After cooling, the reaction mixture is concentrated by rotary evaporator. The residual oil is purified by flash chromatography on silica gel (3: 1 hexanes/EtOAc) to give 1-chloro-6-fluoro-2-aminonaphthalene as a brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert-butyldimethylsilyl chloride; triethylamine; In dichloromethane; for 1h; | Example 20; Synthesis of a compound of Formula (I) where R1, R3, R6, and R(at) are OMe, R(at), R(at), and R10 are Me, R(at) and R5 are OH, R(at) is H, R11 is CN, Y is CH2, and R12 is 6-(5-dimethylaminonaphth-l- ylsulfonylamino)naphth-2-ylcarbonylamino (compound 50); Step 1; To a suspension of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (374 mg, 2.0 mmol) in CH2C12 (8 mL) were added TBDMS-Cl (301 mg, 2.0 mmol) and TEA (1.11 mL, 8.0 mmol) in sequence. After stirring for 1 hr, dansyl-chloride (701 mg, 2.6 mmol) was added to the reaction mixture and stirring was continued for an additional 1 hr. The reaction mixture was diluted with CH2Cl2 (50 mL) and IN HCl (aq). separated organic phase was washed with IN HCl (aq) 50 mL) and sat. NaHCO3 (aq) 50 mL) and concentrated in vacuo. The residue was taken up in THF (3 mL) and treated with 2N NaOH(aq) (10 mL) and MeOH (3 mL). After vigorously stirring for 30 min, IN HCI(aq) was added to adjust the pH of the solution to pH -7. The reaction mixture was concentrated in vacuo and the residue was redissolved in CH2C12 (10 mL) and H20 (10 mL). The aqueous layer was extracted with CH2C12 (3x 20 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo. Precipitation was observed after 3 d and CH2C12 (1 mL) was added to the residue. The precipitation was filtered off and washed with Et20 to afford crude 6-(5-dimethylamino-naphthalene-1-sulfonylamino)-naphthalene-2- carboxylic acid (150 mg, purity 92percent), which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium cyanoborohydride; In methanol; water; at 20℃; for 0.5h; | To a solution of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (1) (Sigma-Aldrich Japan KK) (90%, 3.00 g, 14.4 mmol) in methanol (120 ml) was added sodium cyanotrihydroborate (3.63 g, 57.7 mmol) and formaldehyde (37% in water, 24 ml), and the reaction mixture was stirred at room temperature for 30 min. After evaporation of the solvent, the residue was extracted with water and chloroform. The aqueous layer was acidified to pH 1 with HCl to give a yellow-ochre solid, and extracted with chloroform. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to yield compound (2) (3.23 g, quant.) as a yellow-ochre solid; 1H NMR (DMSO-d6) delta 12.63 (brs, 1H), 8.36 (d, 1H, J=1.5 Hz), 7.88 (d, 1H, J=9.2 Hz), 7.78 (dd, 1H, J=1.8, 8.6 Hz), 7.66 (d, 1H, J=9.0 Hz), 7.26 (dd, 1H, J=2.6, 9.2 Hz), 6.94 (d, 1H, J=2.6 Hz), 3.04 (s, 6H); MS (EI) m/z 215 [M+]; HRMS (EI) calculated for C13H13O2N [M+] 215.0946, found 215.0946. |
95% | With sodium cyanoborohydride; In methanol; at 0 - 25℃; for 2.16667h;Inert atmosphere; | Sodium cyanoborohydride (588mg, 9.34mmol) was added portion-wise to a mixture of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (500mg, 2.67mmol) and formaldehyde (37%, 4.0mL) in methanol (MeOH, 7.0mL) at 0C. After stirring for 10 min at 0C, the mixture was then stirred at room temperature (25C) for 2h. The solvents were removed in vacuo, and the residue was acidified with 1N HCl (aq). Then, the aqueous layer was extracted with ethyl acetate (EtOAc). The collected organic layer was washed with brine, and dried over magnesium sulfate (MgSO4) to afford 6-(N,N-dimethylamino)-2-naphthoic acid 1 (546mg, 95%). The product was used for the next reaction without further purification. 1H NMR (400MHz, DMSO-d6): delta 3.05 (s, 6H), 6.95 (d, J=4.0Hz 1H), 7.26 (dd, J=4.0Hz, 1H), 7.67 (d, J=12.0Hz, 1H), 7.79 (dd, J=4.0Hz, 1H), 7.88 (d, J=12.0Hz, 1H), 8.37 (s, 1H), 12.62 (s, 1H); 13C NMR (400MHz, DMSO-d6): delta 40.4, 105.2, 116.9, 123.6, 125.1, 126.0, 126.2, 130.6, 130.9, 137.5, 150.4, 168.2. HRMS (m/z): [M+H]+calcd. for C13H14NO2, 216.1019; found, 216.1020. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41.5% | With pyridine; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h; | Step-1: 6-Acryloylaminonaphthalene-2-carboxylic acidTo a stirred solution of 2-Amino-6-naphthoic acid (0.3 g, 1.6 mmol) in DMF (2 mL) and pyridine (0.3 mL) was added at 0° C., acryloyl chloride (0.15 g, 1.6 mmol). The resulting mixture was allowed to come to rt and stirred further for 2 h. After that it was poured in water (5 mL) and the solid separated was filtered and dried under reduced pressure to get the desired product (160 mg, 41.5percent) as a pale brown solid. This solid was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 6 6-[({5-[3-Benzyl-8-(trifluoromethyl)quinolin-4-yl]pyridin-3-yl}methyl)amino]-2-naphthoic acid The title compound was prepared from 5-[3-benzyl-8-(trifluoromethyl)quinolin-4-yl]nicotinaldehyde and <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> following the procedure of Example 1 Step 4 as a solid; MS (ES) m/z 564.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; In aq. phosphate buffer; at 80 - 120℃;pH 6 - 7;Microwave irradiation; | General procedure: Sodium 1-amino-4-ar(alkyl)amino-2-sulfoanthraquinone derivatives were synthesized according to described procedures, using a Cu0-catalyzed microwave-assisted Ullmann-coupling reaction. The following general procedure was applied: A 10 mL microwave vial was charged with bromaminic acid sodium salt (7,0.2?1 mmol) and the respective amine (1.25?3 equiv). A buffer solution of Na2HPO4 (pH 9.6, 4.5 mL) and NaH2PO4 (pH 4.2,0.5 mL) and finely powdered elemental copper (0.002?0.003 g, 5-10 mol percent) were then added. The mixture was irradiated in the microwave oven at 80?120°C for 5-24 min (Scheme 1). After cooling to room temperature, ca. 200 mL of water was added to the filtrate and the aqueous solution was extracted 2?3 times with dichloromethane (200 mL). If needed the organic layer was washed with water and NaOH (0.1 N) to enhance transfer of the product to water. The aqueous layer was then concentrated in vacuo to a volume of 10?20 mL, and subsequently submitted to flash column chromatography using a gradient of acetone in water (5?60percent) as the eluent. Fractions containing blue product were collected. The solvent was evaporated by rotary evaporation to remove acetone and reduce the water volume. Complete removal of water was then achieved by lyophilization using a freeze dryer affording the product as a blue powder. For some compounds the last step of purification (RP-18 flash chromatography) had to be repeated two to three times to obtain pure product (P95percent purity as determined by HPLC-UV (254 nm)-ESI-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 9 6-Isothiocyanato-2-naphthoic acid Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (0.28 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 24 hours. To the obtained reaction mixture, a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) was dropwise added over a period of 5 minutes at 0°C, followed by stirring at 0°C for further two hours. Thereafter, 1 M hydrochloric acid (1.5 mL) and sodium sulfite (38 mg, 0.30 mmol) were added and mixed. The formed insoluble matter was collected by filtration and dried under reduced pressure. Then, carbon disulfide (2.0 mL) was added and thoroughly mixed. Then, the insoluble matter was collected by filtration to obtain 6-isothiocyanato-2-naphthoic acid as a cream-colored solid (0.32 g, yield: 96percent, HPLC purity: 94percent, HPLC retention time: 3.7 min). LC-MS ES- 228 (retention time: 4.5 min, condition 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: To a solution of 19 (170 mg, 1 mmol) in 7 mL of DMF was added iPr2NEt (0.7 mL, 4 mmol) and TBTU (350 mg, 1.1 mmol), stirred for 15 min, treated with 32a (0.1 mL, 1.1 mmol) and stirred for 48 h. The mixture was poured into water (50 mL), extracted with EtOAc (2 .x. 75 mL), washed with water and brine, dried (Na2SO4), filtered, and concentrated to afford dark brown solid which was washed with methanol to provide 110 mg of 10a as white powder, Yield 29percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | General procedure: To a solution of 19 (170 mg, 1 mmol) in 7 mL DMF was added iPr2NEt (0.7 mL, 4 mmol) and TBTU (350 mg, 1.1 mmol), stirred for 15 min, treated with aniline (0.1 mL, 1.1 mmol) and stirred for 24 h. The mixture was poured into water (50 mL), extracted with EtOAc (2 .x. 75 mL), washed with water and brine, dried (Na2SO4), filtered, and concentrated to afford a light brown powder which was washed with methanol to provide 90 mg of 9b as white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In methanol; at 75℃; for 12h;Autoclave; | A 25 ml Teflon-lined autoclave containing 6-amino-2-naphthnoic acid (370 mg, 2 mmol), 2-pyridinecarboxaldehyde (210 mg, 2 mmol), and methanol (20 ml) was sealed and heated at 75 °C for 12 h, and then air-cooled slowly for 24 h. The resulting yellow crystals were filtered, and washed with methanol (10 ml × 3) to give ligand (67percent yield). Anal. Calc. for C17H12N2O2: C, 73.90; H, 4.38; N, 10.14. Found: C 74.00; H 4.30; N 10.15percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In methanol; at 75℃; for 12h;Autoclave; | A 25 ml Teflon-lined autoclave containing 6-amino-2-naphthnoic acid (370 mg, 2 mmol), 3-pyridinecarboxaldehyde (210 mg, 2 mmol), and methanol (20 ml) was sealed and heated at 75 °C for 12 h, and then air-cooled slowly for 24 h. The resulting yellow crystals were filtered, and washed with methanol (10 ml × 3) to give ligand (67percent yield). Anal. Calc. for C17H12N2O2: C, 73.90; H, 4.38; N, 10.14. Found: C 74.00; H 4.30; N 10.15percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
323 mg | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 3.5h;Inert atmosphere; | EXAMPLE 4 SYNTHESIS OF PROBE COMPOUND, DYn-Naph [0147] The DYn-Naph compound (FIG. 5) may be synthesized by the following method (FIG. 6A, Scheme 2). To a dry round bottom flask flushed with nitrogen was added 6-amino-2-napthoic acid (200 mg, 1.07 mmol), NHS (135.18 mg, 1.17 mmol), and dry DMF (2 mL). The reaction mixture was cooled in an ice-bath. EDC-HC1 (224.71 mg, 1.17 mmol) was added and the reaction mixture was allowed to react at 0 °C for 30 min, then the reaction was brought up to room temperature and allowed to mix for an additional 3 hrs. The reaction was quenched with the addition of saturated sodium bicarbonate and extracted with EtOAc. The organic layer was dried over MgS04, filtered, and concentrated for the next step. To a dry round bottom flask flushed with nitrogen was added the NHS-ester of Intermediate Compound (1) (323 mg, 1.13 mmol), which was suspended in dry DMF (4 mL). 4-pentyneamine (292.5 mg, 3.52 mmol) and DIPEA (613 uL, 3.52 mmol) were subsequently added and the reaction mixture was allowed to mix at 75 °C overnight under nitrogen. The reaction was quenched with the addition of saturated sodium bicarbonate and extracted with EtOAc. The organic layer was dried over MgS04, filtered, and concentrated. Flash column chromatography was used for purification (1 : 1 EtOAc:Hexanes, 10percent MeOH in EtOAc spiked with 1percent TEA) to yield 188.2 mg of Intermediate Compound (2) (70percent yield). To a dry round bottom flask flushed with nitrogen was added 3-methoxy-5-oxocyclohex-3-9-enecarboxylic acid (115.39 mg, 0.678 mmol), EDC-HC1 (194.48 mg, 1.02 mmol), and DMAP (99.4 mg, .813 mmol). The flask was sealed under nitrogen. Intermediate Compound (2) (188.2 mg, 0.746 mmol) was resuspended in dry DMF (2 mL) and added to the reaction mixture followed by the addition of TEA (95 mu, 0.678 mmol). The reaction mixture was brought up to 85 °C and allowed to mix overnight under nitrogen. The reaction was quenched with the addition of water and extracted with EtOAc. The organic phases were combined and dried over MgS04, filtered, and concentrated. Flash column chromatography was used for purification (1 : 1 Hexanes:EtOAc, 7:3 EtOAc:Hexanes, 5percent MeOH in EtOAc) to yield 138.1.6 mg of product (46percent yield). In a round bottom flask, Intermediate Compound (3) (138.1 mg, 0.34 mmol) was suspended in a 1 : 1 Acetonitrile:Water solution (5 mL). 10percent> CAN (18.8 mg, 0.034 mmol) was added and the reaction mixture was refluxed at 95 °C for 3 hrs., resulting in the synthesis of DYn-Naph (FIG. 5). The reaction was then cooled and concentrated and directly purified by HPLC. |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 3.5h;Inert atmosphere; | To a dry round bottom flask flushed with nitrogen was added 6-amino-2-napthoic acid (200 mg, 1.07 mmol), NHS (135.18 mg, 1.17 mmol), and dry DMF (2 mL). The reaction mixture was cooled in an ice-bath. EDC-HCl (224.71 mg, 1.17 mmol) was added and the reaction mixture was allowed to react at 0 °C for 30 min, then the reaction was brought up to rt and allowed to mix for an additional 3 hrs. The reaction was quenched with the addition of saturated sodium bicarbonate and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated for the next step without further purification. To a dry round bottom flask flushed with nitrogen was added the NHS-ester (323 mg, 1.13 mmol) which was suspended in dry DMF (4 mL). 4-pentyneamine (292.5 mg, 3.52 mmol) and DIPEA (613 uL, 3.52 mmol) were subsequently added and the reaction mixture was allowed to mix at 75 °C overnight under nitrogen. The reaction was quenched with the addition of saturated sodium bicarbonate and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated. Flash column chromatography was used for purification (1:1 EtOAc:Hexanes, 10percent MeOH in EtOAc spiked with 1percent TEA) to yield 188.2 mg of (5) (70percent yield over 2 steps) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With N-chloro-succinimide; In tetrachloromethane; for 1h;Reflux; | 6-Amino-5-chloro-2 -naphthoic acid: 6-Amino-2 -naphthoic acid (0.17 g, 0.9 mmol), N- chlorosuccinimide (0.12 g, 1 eq), and carbon tetrachloride (25 mL) were combined in a round bottom flask, and heated under reflux for lh. After cooling to rt, the solid was filtered. The subsequent crude materials were added directly to KP-Sil? columns (10 g) with products separating from impurities using an isocratic solvent system CH2Cl2:MeOH (1 : 19), on the Biotage®-Isolera Four instrument, monitoring UV Trace at 254/365 nm. The 0.9 mmol scale yielded 120 mg of white microcrystals after chromatography (mp = 274-276°C decomp, 60percent yield). 1H NMR (D6-DMSO) delta 6.14 (s, 2H), 7.19 (d, J = 8.8 Hz, 1H), 7.85 (dd, J= 42.2, 8.8 Hz, 1H), 7.94 (d, J = 1.7 Hz, 1H), 7.96 (d, J = 1.7 Hz, 1H), 8.39 (d, J = 1.7 Hz, 1H), 12.78 (s, 1H). 13C NMR (D6-DMSO) 107.5, 118.9, 121.1, 123.5, 125.8, 126.9, 129.3, 130.9, 133.8, 145.0, 167.5. LCMS t = 4.2 min, Calcd for CnH9ClN02; CnH8ClNNa02 222.03; 244.01 [M+H]+; [M+Na]+, Found 222.09; 244.06. |
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P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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