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CAS No. : | 10172-35-7 | MDL No. : | MFCD18088521 |
Formula : | C7H7BrN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYCRRMSGEDGSFS-UHFFFAOYSA-N |
M.W : | 247.05 | Pubchem ID : | 21938204 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.86 |
TPSA : | 81.07 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.19 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 2.28 |
Log Po/w (WLOGP) : | 1.96 |
Log Po/w (MLOGP) : | 0.81 |
Log Po/w (SILICOS-IT) : | -0.34 |
Consensus Log Po/w : | 1.28 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.02 |
Solubility : | 0.237 mg/ml ; 0.00096 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.62 |
Solubility : | 0.0593 mg/ml ; 0.00024 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.4 |
Solubility : | 0.972 mg/ml ; 0.00394 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.5 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With bromine; In dichloromethane; at -20.0℃; | To a solution of 4-methoxy-2-nitrobenzenamine (6.72 g, 40 mmol) in DCM (70 mL) at -20 C, bromine (2.50 mL, 48 mmol) was added dropwise. The mixture was stirred at -20 C for 30 min. The mixture was poured into ice-water. The pH was adjusted to 8 with saturated sodium bicarbonate aqueous solution and then extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM/petroleum ether = 1 :2) to yield the product (6.42 g, 65% yield). ESI-MS m/z: 247.0 [M +H]+. |
With bromine; In dichloromethane; | Reference Example 17 Synthesis of 2-bromo-4-methoxy-6-nitroaniline To a solution of 4-methoxy-2-nitroaniline (35 g) in dichloromethane (350 mL) was subsequently added dropwise bromine (12.9 mL) at -20 C. After stirring for 30 minutes at the same temperature, this was poured into ice water, adjusted to pH 7 to 8 with saturated sodium bicarbonate aqueous solution and then extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). After concentration of the desired fraction, the resulting residue was crystallized from hexane and ethyl acetate and then collected by filtration to obtain the title compound as reddish orange crystals (29.6 g). NMR (CDCl3) delta [ppm]: 7.63 (1H, d, J=3 Hz), 7.44 (1H, d, J=3 Hz), 6.38 (2H, bs), 3.80 (3H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide; In 1-methyl-pyrrolidin-2-one; | Reference Example 18 Synthesis of 2-amino-5-methoxy-3-nitrobenzonitrile To a solution of <strong>[10172-35-7]2-bromo-4-methoxy-6-nitroaniline</strong> (45 g) obtained in Reference Example 17 in N-methyl-2-pyrrolidone (225 mL) was subsequently added copper(I) cyanide (33 g). This was stirred at 150 C. for 5.5 hours. After spontaneous cooling, aqueous ammonia was added to the mixture and the resulting mixture was stirred for 20 minutes, and then insoluble material was separated by filtration. The thus separated residue was washed with ethyl acetate, and the filtrate and washed solution were combined to carry out separation of layers. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under a reduced pressure to obtain the title compound as crystal (14.1 g). NMR (CDCl3) delta [ppm]: 7.90 (1H, d, J=3 Hz), 7.38 (1H, d, J=3 Hz), 6.45 (2H, bs), 3.83 (3H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With thiophene; hydrogen;platinum on carbon; In methanol; di-isopropyl ether; at 25.0℃;Inert atmosphere; | MeOH (150 ml) was added to Pt/C 5 % (1 g) under N2 atmosphere. Subsequently, a 0.4 % thiophene sol. in DIPE (2 ml) and <strong>[10172-35-7]2-bromo-4-methoxy-6-nitroaniline</strong> (5 g, 20.2 mmol) were added. The r.m. was stirred at 25 0C under H2 atmosphere until 3 eq ofH2 was absorbed. The catalyst was filtered off over diatomaceous earth and the filtrate was concentrated in vacuo. Yield: 4.33 g of intermediate 105 (99 %), which was used as such in the next step. |
99% | With thiophene; hydrogen;platinum on carbon; In methanol; di-isopropyl ether; at 25.0℃; | Example A30 a) Preparation of intermediate 78MeOH (150 ml) was added to Pt/C 5 % (1 g) under N2 atmosphere. Subsequently, a 0.4 % thiophene sol. in DIPE (2 ml) and <strong>[10172-35-7]2-bromo-4-methoxy-6-nitroaniline</strong> (5 g, 20.2 mmol) were added. The r.m. was stirred at 25 0C under H2 atmosphere until 3 eq of H2 was absorbed. The catalyst was filtered off over diatomaceous earth and the filtrate was concentrated in vacuo. Yield: 4.33 g of intermediate 78 (99 %), which was used as such in the next reaction step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tert.-butylnitrite; copper dichloride; In acetonitrile; at 60.0℃; | To a solution of t-Butyl nitrite (3.75 g, 36.4 mmol) and CuCl2 (3.92 g, 29.2 mmol) in acetonitrile (120 mL) at 60 C, was added 2-bromo-4-methoxy-6- nitrobenzenamine (6.0 g, 24.3 mmol) and the resulting mixture was stirred at 60 C overnight. The mixture was concentrated in vacuo. The residue was dissolved in DCM (100 mL), washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM/petroleum ether = 1 :3) to yield the product (5.01 g, 77% yield). |
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