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Chemical Structure| 206548-13-2
Chemical Structure| 206548-13-2
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Product Details of [ 206548-13-2 ]

CAS No. :206548-13-2 MDL No. :MFCD05664860
Formula : C8H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RWLPKYJTGUCBQH-UHFFFAOYSA-N
M.W : 230.06 Pubchem ID :11850383
Synonyms :

Calculated chemistry of [ 206548-13-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.47
TPSA : 63.32 Ų

Pharmacokinetics

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) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 1.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.199 mg/ml ; 0.000864 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.105 mg/ml ; 0.000457 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.504 mg/ml ; 0.00219 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 206548-13-2 ]

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:

Application In Synthesis of [ 206548-13-2 ]

* 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.

  • Upstream synthesis route of [ 206548-13-2 ]
  • Downstream synthetic route of [ 206548-13-2 ]

[ 206548-13-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 4389-45-1 ]
  • [ 206548-13-2 ]
YieldReaction ConditionsOperation in experiment
97% at 20 - 25℃; General procedure: Bromine (3.43 mL, 130 mmol) was added to a solution of 2-amino-5-trifluoromethylbenzoic acid ethyl ester (5.34 g, 23 mmol) in DCM (26.5 mL) at room temperature.
A saturated aqueous sodium thiosulfate solution (30 mL) was added thereto under ice-cooling, and extraction was performed with ethyl acetate.
The extract was washed with brine and then dried over anhydrous sodium sulfate.
The drying agent was removed by filtration, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.97 g, 97percent) as a pale yellow oily substance. The title compound was synthesized from 2-amino-3-methyl-benzoic acid under the same conditions as for Compound a9. However, acetic acid was used in place of DCM as a solvent.
85% With hydrogen bromide In water; dimethyl sulfoxide at 20℃; Step A: To a solution of 2-amino-3-methylbenzoic acid (10.0 g, 66 mmol) in DMSO was added 48percent aqueous hydrogen bromide (18.0 ml). The reaction solution was stirred at room temperature overnight and then quenched with saturated sodium bicarbonate. The resultant mixture was stirred overnight. Precipitation was collected by filtration and dried in vacuo to give 2-amino-5-bromo-3-methylbenzoic acid (13.0 g,85percent) as a pink solid: 1H NMR (500 MHz, DMSO) δ 7.69 (d, J = 1.0 Hz, 1 H), 7.33 (d, J = 1.0 Hz, I H), 2.10 (s, 3 H); MS (ESI+) m/z 231 (M+H).
85%
Stage #1: With bromine In acetic acid at 0 - 20℃; for 0.583333 h;
Stage #2: With sodium carbonate In dichloromethane; water; acetic acid
Stage #3: With hydrogenchloride In water
To a solution of 2-amino-3-methylbenzoic acid (5.00 g, 33.1 mmol) in acetic acid (110 mL) at 0 0C was added drop wise a mixture of bromine (1.7 mL, 33 mmol) in acetic acid (50 mL) over about 5 minutes. Following addition, the cooling bath was removed and the mixture was stirred at room temperature for 30 minutes before removal of acetic acid under reduced pressure. The mixture was diluted with CH2CI2 and washed with saturated aqueous Na2CO3. The aqueous phase was back extracted with CH2CI2. The ~aqueoOs phrase'was acidified-using concentrated HCI to pH 7:2rwith intense foaming observed. Copious amounts of precipitate formed and were isolated by vacuum filtration . The filtrate was further acidified with concentrated HCI to pH 6.3 and a second crop of precipitate was collected. The combined solids were dried at 65 0C /0.5 mmHg to provide 2-amino-5-bromo-3-methylbenzoic acid (6.43 g, 85percent).A solution of 2-amino-5-bromo-3-methylbenzoic acid (6.43 g, 27.9 mmol) in DMF (93 mL) containing cesium carbonate (13.7 g, 41.9 mmol) was stirred at room temperature for 40 minutes before drop wise addition of a solution of iodomethane (1.7 mL, 28 mmol) in DMF (21 mL). The mixture was stirred at room temperature for 2 days. The mixture was diluted with water (300 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to afford a brown oil that solidified into a beige solid after drying at room temperature/0.5 mmHg to provide methyl 2-amino- 5-bromo-3-methylbenzoate (5.45 g, 80percent).To a solution of methyl 2-amino-5-bromo-3-methylbenzoate (5.45 g, 22.3 mmol) in CHCI3 (64 mL) was added acetic anhydride (4.9 mL) at such rate as to maintain the internal temperature below 40 0C. The <n="31"/>resulting mixture was stirred at room temperature for 1 hour and then potassium acetate (0.66 g, 6.7 mmol) and isoamyl nitrite (6.6 ml_, 49 mmol) were added. The reaction mixture was heated at reflux overnight and then cooled to room temperature and concentrated. The residue was dissolved in methanol (22 mL) and 6 N HCI (22 mL) and stirred at room temperature for about 4 hours. A yellow solid was isolated by vacuum filtration and rinsed with water. The solids were dried at 65 C/0.5 mmHg to provide methyl δ-bromo-IH-indazole^-carboxylate (4.90 g, 86percent).To a solution of δ-bromo-IH-indazole^-carboxylate (250 mg, 0.98 mmol) in methanol (2 mL) at 0 0C was added 30percent aqueous KOH (0.15 g KOH in 0.5 mL water). The mixture was stirred at room temperature for 2 days. The resultant solids were isolated by vacuum filtration and rinsed with MeOH. The solid material was dried at 65 0C /0.5 mmHg to provide the title compound as a light yellow solid (182 mg, 67 percent).
83% With N-Bromosuccinimide In N,N-dimethyl-formamide for 3 h; Reflux General procedure: In a 100ml of round flask , add 20ml of 3-methyl-2-amino-benzoic acid, 50ml of DMF,30ml mmol of N- chlorosuccinimide(or N- bromosuccinimide ) and after stirred atreflux for 3h, the reaction solution was poured into ice water and dilutehydrochloric acid acidifying to pH = 6. Filtered andthe resulting solid was washed small amount of ethanol to give a gray solidchlorinated or brominated anthranilate III.yield 83percent. Y selected from :cholrine and bromine.
83% With N-Bromosuccinimide In N,N-dimethyl-formamide for 3 h; To a 100 ml round bottom flask was added 3.0 g of 20 mmol 3-methyl-2-aminobenzoic acid X,30 ml of DMF,6.7 grams of 30 millimoles of NCS (or 30 millimoles of NBS),After stirring for 3 hours,The reaction solution was poured into ice water,Dilute hydrochloric acid to pH = 6,filter,The resulting solid was washed with a small amount of ethanol to give 2-amino-3-methyl-5-halo-benzoic acid III,Gray solid,4.6 grams or more,Yield is greater than 83percent.Y selected from:chlorine,bromine,The 2-amino-3-methyl-5-halo-benzoic acid III is selected from the group consisting of -2-amino-3-methyl-5-chlorobenzoic acid,2-amino-3-methyl-5-bromo-benzoic acid
52.2% at 0 - 20℃; for 4 h; To a solution of 19-51 (15 g, 0.1 mol) in AcOH (80 mL) was added Br2 (5.1 mL, 0.1 mol) dropwise at 0 °C. The reaction mixturewas stirred at room temperature for 4 h. The mixture was diluted with EtOAc and basified with aqueous NaOH solution (4 N) to pH 7. The mixture was extracted with EtOAc, dried, and concentrated to afford the crude product, which was purified by column chromatography on silica gel (eluted with DCMIMeOH = 100:0 to 50:1) to afford 19-S2 (12.0 g, 52.2percent yield) as a white solid. LC/MS (ESI) m/z: 230 (M+H).
51% With hydrogen bromide In dimethyl sulfoxide at 20℃; Method AZ: 2-Amino-5-bromo-3-methylbenzoic acid (lvi-a)
To a solution of 2-amino-3-methylbenzoic acid (1.23 g, 8.14 mmol, 1.0 eq) in 15 mL of DMSO was added 40percent HBr (6.00 mL, 44.7 mmol, 5 eq).
The resulting mixture was stirred at room temperature overnight.
A white precipitate formed during the course of the reaction.
The reaction mixture was quenched with saturated aqueous NaHCO3 resulting in a white solid that was filtered and dried in vacuo to yield 950 mg in 51percent yield of lvi-a as white solid. LCMS m/z=229.9 (M+1) (Method B) (retention time=1.20 min).
51% With hydrogen bromide In dimethyl sulfoxide at 20℃; 40percent HBr (6.00 mL, 44.7 mmol, 5 eq) was added to a solution of 2-amino-3-methylbenzoic acid (1.23 g, 8.14 mmol, 1.0 eq) in DMSO (15 mL).The resulting mixture was stirred at room temperature overnight. A white precipitate formed during the course of the reaction.The reaction mixture was quenched with saturated aqueous NaHCO 3 to give a white solid,This was filtered and dried under vacuum to obtain 950 mg (51percent yield) of lvi-a as a white solid. LCMS m / z = 229.9 (M + 1) (Method B) (retention time = 1.20 min).
95% With bromine In acetic acid Example 132
2-Amino-5-bromo-3-methyl-benzoic acid
To a mixture of 1.5g (10mmol) of 3-methyl-2-amino benzoic acid in 50mL of glacial acetic acid was added 1.6 g (10 mmol) of bromine and the resulting mixture was stirred at room temperature for 5 h.
The reaction mixture was then poured into water and the precipitated solid was filtered, washed with water and air dried to provide 2.2g (95percent) of the desired product as a brown solid. m.p.245°C. Electrospray Mass Spec 232 (M+H).

Reference: [1] Patent: EP2842946, 2015, A1, . Location in patent: Paragraph 0309; 0728; 0729
[2] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 44, p. 10942 - 10951
[3] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5921 - 5929
[4] Patent: WO2011/8572, 2011, A2, . Location in patent: Page/Page column 70
[5] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 29-30
[6] Patent: CN103450154, 2016, B, . Location in patent: Paragraph 0063-0065
[7] Patent: CN104031026, 2017, B, . Location in patent: Paragraph 0051; 0052; 0053; 0054
[8] Patent: WO2018/160889, 2018, A1, . Location in patent: Page/Page column 474
[9] Patent: US2015/307477, 2015, A1, . Location in patent: Paragraph 1616
[10] Patent: JP6121658, 2017, B2, . Location in patent: Paragraph 1383; 1385
[11] Patent: US5929097, 1999, A,
[12] Patent: EP938471, 2001, B1,
[13] Patent: WO2014/160177, 2014, A2, . Location in patent: Paragraph 00252
[14] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 3, p. 865 - 875
  • 2
  • [ 77395-10-9 ]
  • [ 206548-13-2 ]
YieldReaction ConditionsOperation in experiment
75% With dihydrogen peroxide; sodium chloride; sodium hydroxide In water at 0℃; for 1.5 h; Step 4: 2-amino-5-bromo-3-methylbenzoic acidA mixture of 5-bromo-7-methylindoline-2,3-dione (8 g, 0.033 mol), sodium chloride (4.5 g, 0.09 mol) and sodium hydroxide (3.6 g, 0.09 mol) was dissolved in water (96 mL) with stirring to give a yellow solution. The reaction mixture was cooled to 0°C and to this mixture was added slowly a solution of 30percent hydrogen peroxide (7 mL) and .sodium hydroxide (6.27 g) in 83 mL of water. The reaction mixture was stirred for another 1.5 h at 0°C and then quenched with glacial acetic acid to give a tan precipitate. The solid was filtered, washed thoroughly with cold water and dried under vacuum to afford the title compound (5.8 g, 75percent).XH NMR (400 MHz, DMSO-d6) : δ 7.69 (d, J = 2.4 Hz, 1H), 7.26 (s, 1H), 2.0 (s, 3H); ESI-MS : Calculated mass: 228.97; Observed mass: 228.10 [M-H]\
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5921 - 5929
[2] Patent: WO2014/169167, 2014, A1, . Location in patent: Page/Page column 81; 82
  • 3
  • [ 5437-38-7 ]
  • [ 206548-13-2 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5921 - 5929
[2] Patent: US2015/307477, 2015, A1,
[3] Patent: JP6121658, 2017, B2,
  • 4
  • [ 1127-59-9 ]
  • [ 206548-13-2 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5921 - 5929
[2] Patent: WO2014/169167, 2014, A1,
  • 5
  • [ 95-53-4 ]
  • [ 206548-13-2 ]
Reference: [1] Patent: WO2014/169167, 2014, A1,
  • 6
  • [ 206548-13-2 ]
  • [ 74-88-4 ]
  • [ 206548-14-3 ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Step B: To a solution of 2-amino-5-bromo-3-methylbenzoic acid (3.0g, 13 mmol) from Step A above in DMF was added cesium carbonate (6.4g, 20 mmol) followed by iodomethane (0.8 ml, 13 mmol). The reaction was stirred at ambient temperature overnight. The mixture was washed with water and extracted with dichloromethane. The organic extract was dried (Na2SO4) and concentrated in vacuo to afford methyl 2-amino-5-bromo-3-methylbenzoate (3.2g, 100percent) as a grey solid: 1H NMR (500 MHz, CDCl3) δ 7.89 (d, J = 2.4 Hz, IH), 7.28 (d, J = 2.1 Hz, IH), 5.84 (brs, 2H), 3.87 (s, 3H), 2.15 (s, 3H); MS (ES1+) m/z 245 (M+H).
92.8% With potassium carbonate; silver(l) oxide In acetone at 20 - 30℃; for 18 h; To a 500 mL round-bottom flask, 0.2 mol of2-amino-3-methyl-5-bromobenzoic acid having the structural formula of IV-2, 200 mL of acetone, 2 grams of potassium carbonate and 0.5 gram of silver oxide were added, stirred at room temperature for 0.5 hour, 0.3 mmol of methyl iodide was dripped, and reacted at a temperature range of 20-30° C. for 18 hours, filtered to remove the solid, washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, the solvent was removed to obtain 45.3 grams of an intermediate of 2-amino-3-methyl 5-bromoben- zoic acid methyl ester having a structural formula of VIII-2, and the yield was 92.8percent;
89%
Stage #1: With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1 h; Inert atmosphere
Stage #2: for 24.5 h;
[0393j 2-Amino-5-bromo-3-methylbenzoic acid (5.0 g, 21.7 mmol)in dry DMF (35 mL) was stirredwith Cs2CO3 (10.62 g, 32.6 mmol) at room temperature for lh under nitrogen. lodomethane (3.4 g, 1.5 mL, 23.95 mmol) in dry DMF (7 ml) was added dropwise to the above stirring reaction mixture over a period of 30 mm and continued the reaction for 24 h. Reaction mixture was diluted with water (200 mL) and stirred to observe hetergeneous suspension. The purple solid was collected by filtration and dried to obtain methyl 2-amino-5-bromo-3- methylbenzoate (4.72 g, 89percent).’H NMR (DMSO-d6): ö 7.67 (app d, 1H, J = 2.1 Hz), 7.34 (s, 1H), 6.60 (s, 2H), 3.78 (s, 3H), 2.09 (s, 3H). LCMS: rt 7.98 mm (A), purity 99 percent, MS (mle) 245 (MHj.
86.6% With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 16 h; To a solution of 19-S2 (12 g, 52.2 mmol) in DMF (60 mL) was added Cs2CO3 (25.5 g, 78.3 mmol) and CH3I (7.79 g, 54.8mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. The mixture was then diluted with EtOAc, washed with 5percent aqueous LiC1 solution and brine, dried, and concentrated to afford the crude product, which was purified by column chromatography on silica gel (eluted with PE/EtOAc = 50:1 to 20:1) to afford 19-S3 (11.0 g, 86.6percent yield) as a white solid.LC/MS (ESI) m/z: 244 (M+H)t
80%
Stage #1: With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667 h;
Stage #2: at 20℃; for 48 h;
To a solution of 2-amino-3-methylbenzoic acid (5.00 g, 33.1 mmol) in acetic acid (110 mL) at 0 0C was added drop wise a mixture of bromine (1.7 mL, 33 mmol) in acetic acid (50 mL) over about 5 minutes. Following addition, the cooling bath was removed and the mixture was stirred at room temperature for 30 minutes before removal of acetic acid under reduced pressure. The mixture was diluted with CH2CI2 and washed with saturated aqueous Na2CO3. The aqueous phase was back extracted with CH2CI2. The ~aqueoOs phrase'was acidified-using concentrated HCI to pH 7:2rwith intense foaming observed. Copious amounts of precipitate formed and were isolated by vacuum filtration . The filtrate was further acidified with concentrated HCI to pH 6.3 and a second crop of precipitate was collected. The combined solids were dried at 65 0C /0.5 mmHg to provide 2-amino-5-bromo-3-methylbenzoic acid (6.43 g, 85percent).A solution of 2-amino-5-bromo-3-methylbenzoic acid (6.43 g, 27.9 mmol) in DMF (93 mL) containing cesium carbonate (13.7 g, 41.9 mmol) was stirred at room temperature for 40 minutes before drop wise addition of a solution of iodomethane (1.7 mL, 28 mmol) in DMF (21 mL). The mixture was stirred at room temperature for 2 days. The mixture was diluted with water (300 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to afford a brown oil that solidified into a beige solid after drying at room temperature/0.5 mmHg to provide methyl 2-amino- 5-bromo-3-methylbenzoate (5.45 g, 80percent).To a solution of methyl 2-amino-5-bromo-3-methylbenzoate (5.45 g, 22.3 mmol) in CHCI3 (64 mL) was added acetic anhydride (4.9 mL) at such rate as to maintain the internal temperature below 40 0C. The <n="31"/>resulting mixture was stirred at room temperature for 1 hour and then potassium acetate (0.66 g, 6.7 mmol) and isoamyl nitrite (6.6 ml_, 49 mmol) were added. The reaction mixture was heated at reflux overnight and then cooled to room temperature and concentrated. The residue was dissolved in methanol (22 mL) and 6 N HCI (22 mL) and stirred at room temperature for about 4 hours. A yellow solid was isolated by vacuum filtration and rinsed with water. The solids were dried at 65 C/0.5 mmHg to provide methyl δ-bromo-IH-indazole^-carboxylate (4.90 g, 86percent).To a solution of δ-bromo-IH-indazole^-carboxylate (250 mg, 0.98 mmol) in methanol (2 mL) at 0 0C was added 30percent aqueous KOH (0.15 g KOH in 0.5 mL water). The mixture was stirred at room temperature for 2 days. The resultant solids were isolated by vacuum filtration and rinsed with MeOH. The solid material was dried at 65 0C /0.5 mmHg to provide the title compound as a light yellow solid (182 mg, 67 percent).

Reference: [1] Patent: WO2011/8572, 2011, A2, . Location in patent: Page/Page column 70-71
[2] Patent: US2015/322037, 2015, A1, . Location in patent: Paragraph 0052; 0053; 0054
[3] Patent: WO2015/157093, 2015, A1, . Location in patent: Paragraph 0393
[4] Patent: WO2018/160889, 2018, A1, . Location in patent: Page/Page column 474; 475
[5] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 29-30
  • 7
  • [ 206548-13-2 ]
  • [ 206548-14-3 ]
Reference: [1] Patent: US5929097, 1999, A,
[2] Patent: EP938471, 2001, B1,
[3] Chinese Journal of Chemistry, 2012, vol. 30, # 8, p. 1748 - 1758
  • 8
  • [ 67-56-1 ]
  • [ 206548-13-2 ]
  • [ 206548-14-3 ]
YieldReaction ConditionsOperation in experiment
1.1 g for 72 h; Reflux The above filter cake was taken into methanol (100 mL) followed by addition of concentrated sulfuric acid (2 mL), then heated to reflux over 72 hours. On cooling to room temperature, the solution was concentrated, and the residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed twice with additional saturated aqueous sodium bicarbonate then dried over anhydrous sodium sulfate, filtered, and concentrated to afford methyl 2-amino-5-bromo-3-methylbenzoate ( 1.1 g) as a colorless solid. GCMS for C9H,oBrN02: 245 (M+).
Reference: [1] Patent: WO2014/160177, 2014, A2, . Location in patent: Paragraph 00253
  • 9
  • [ 206548-13-2 ]
  • [ 898747-24-5 ]
Reference: [1] Patent: WO2015/157093, 2015, A1,
[2] Patent: WO2018/160889, 2018, A1,
[3] Patent: WO2008/65508, 2008, A1,
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