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Product Details of [ 20776-50-5 ]

CAS No. :20776-50-5 MDL No. :MFCD03618454
Formula : C7H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BNNICQAVXPXQAH-UHFFFAOYSA-N
M.W : 216.03 Pubchem ID :88691
Synonyms :
4-Bromoanthranilic Acid

Calculated chemistry of [ 20776-50-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.51
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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 1.18
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.18
Solubility : 1.41 mg/ml ; 0.00653 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 2.26 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.27
Solubility : 1.16 mg/ml ; 0.00536 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 20776-50-5 ]

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 [ 20776-50-5 ]

* 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 [ 20776-50-5 ]
  • Downstream synthetic route of [ 20776-50-5 ]

[ 20776-50-5 ] Synthesis Path-Upstream   1~42

  • 1
  • [ 20776-50-5 ]
  • [ 77287-34-4 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
89% at 170℃; for 12 h; 0.0 g (1.56 mol) of   2-amino-4-bromobenzoic acid were suspended in 970 ml of   formamide and subsequently stirred at 170° C. for 12 h. Conventional work-up gave 326.0 g of   7-bromo-3H-quinazolin-4-one; HPLC/MS (M+H)+=226 as solid.
71% at 140 - 145℃; for 4 h; 7-bromoquinazolin-4(3H)-oneA mixture of 2-amino-4-bromobenzoic acid (2.0 g) and formamide (1.5 ml) was stirred while heating at 140-145 C. After 4 hours, the reaction mixture was cooled, and 30 ml of water was added causing a solid to precipitate. After collection by filtration, the crude product was pure enough to be used in the next step without further purification. Yield: 1.47 g (6.53 mmol, 71percent). 1H NMR (250 MHz, DMSO) ? (ppm) 8.14 (d, J= 3.0 Hz, 1 H), 8.05 (d, J= 8.5 Hz, 1 H), 7.90 (d, J= 1.9 Hz, 1 H), 7.70 (dd, J= 1.9 Hz, J= 8.5 Hz, 1 H).
36.3% at 150℃; for 1.45 h; Microwave irradiation; Inert atmosphere 2-amino-4-bromobenzoic acid (Compound 4) was reacted with formamide to give 7-bromoquinazolin-4 (3H) -one (Compound 5)5.0 g (23.14 mmol) of 2-amino-4-bromobenzoic acid (Compound 4) was dissolved in 80 ml (2. Olmmol) formamide, Under the protection of nitrogen at 150 ° C, power 300W microwave conditions, reaction 1.45h, after the end of the reaction, the reaction solution by adding ice water, And the mixture was extracted three to four times with ethyl acetate. The extracted organic phase was washed successively with a saturated sodium hydrogencarbonate solution and saturated brine,Dried over sodium sulphate and dried to give a reddish-brown residue, which was chromatographed to give a red brown solid, 7-bromoquinazolin-4 (3H) -one (compound 5), 1.898 in 36.3percent yield;
10.5 g at 190℃; for 10 h; 7-Bromoquinazolin-4(3H)-one (compound A.1)
2-Amino-4-bromobenzoic acid (15.5 g) was dissolved in 100 mL of formamide and the solution was heated at 190° C. for 10 h.
After the reaction was cooled to room temperature, the solid was collected via filtration, rinsed with water, and dried to give 10.5 g of 7-bromo-4-quinazolinone, LCMS ESI(+) m/z: 225/227 (M+1).

Reference: [1] Patent: US2013/12489, 2013, A1, . Location in patent: Paragraph 0182
[2] Patent: WO2010/146173, 2010, A1, . Location in patent: Page/Page column 16
[3] Patent: CN105503744, 2016, A, . Location in patent: Paragraph 0033; 0036; 0037
[4] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[5] Patent: US2016/31860, 2016, A1, . Location in patent: Paragraph 0110; 0111
[6] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 373 - 385
[7] Patent: CN107814773, 2018, A, . Location in patent: Paragraph 0064-0065
  • 2
  • [ 20776-50-5 ]
  • [ 3473-63-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
98% for 13 h; Heating / reflux 3) Formamidine acetate (1.96 g, 18.9 mmol) and 2-ethoxyethanol (25 mL) were added to 4-bromoanthranyl acid (1.63 g, 7.55 mmol) and the mixture was heated under reflux for 7 hrs. Formamidine acetate (1.45 g) was added and the mixture was further refluxed for 6 hrs. Dilute aqueous ammonia solution (30 mL) was added, and after stirring for a while, the product was collected by filtration and dried to give the objective 7-bromo-3H-quinazolin-4-one (1.67 g, 98percent). [CHEMMOL-00362] [0144] 1H NMR (DMSO-d6) δ ppm: 7.69 (dd, J=1.9, 8.4 Hz, 1H), 7.89 (d, J=1.9 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 8.14 (br s, 1H).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 31
  • 3
  • [ 194851-17-7 ]
  • [ 20776-50-5 ]
  • [ 194851-16-6 ]
Reference: [1] Patent: US5814630, 1998, A,
  • 4
  • [ 20776-50-5 ]
  • [ 68-12-2 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
36.3% at 150℃; for 1.45 h; Inert atmosphere; Microwave irradiation (23.14 mmol) of 2-amino-4-bromobenzoic acid was dissolved in 80 ml (2.01 mmol) of formamide and reacted under nitrogen at 150 ° C under a microwave power of 300 W for 1.45 h. After completion of the reaction, The reaction solution was added to ice water and extracted with ethyl acetate for 3-4 times. The extracted organic phase was washed successively with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then spin dried to give a reddish brown residue , And the reddish brown residue was separated on a chromatographic column to give 1.89 g of a reddish brown solid 7-bromoquinazolin-4 (3H) -one in 36.3percent yield.
Reference: [1] Patent: CN105859638, 2016, A, . Location in patent: Paragraph 0036; 0037
  • 5
  • [ 20776-50-5 ]
  • [ 114306-17-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1912, vol. 388, p. 34
  • 6
  • [ 32315-10-9 ]
  • [ 20776-50-5 ]
  • [ 76561-16-5 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 16 h; Inert atmosphere; Reflux Example 7; 2-Amino-1-ethyl-4-oxo-7-[4-(3-pyridin-3-ylmethylureido)phenyl]-1,4-dihydroquinoline-3-carboxylic Acid Amide (No. 57)7.1: 7-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 5.0 g (23.1 mmol) of 2-amino-4-bromobenzoic acid are dissolved in 50 ml of anhydrous dioxane. The temperature of the mixture is reduced to 0° C. by means of an ice bath. 2.3 g (7.6 mmol) of triphosgene are added dropwise. The ice bath is replaced with an oil bath and the mixture is refluxed for 16 h. After a return to ambient temperature, water (100 ml) is added and the precipitate formed is filtered off, washed with Et2O (3.x.25 ml) and then dried in an oven, so as to obtain 5.6 g (23.1 mmol) of the compound in the form of a beige powder. Yield=100percent. 1H NMR DMSO d6 (300 MHz) 7.29 (d, J=1.8 Hz, 1H); 7.41 (dd, J=8.4 Hz, J=1.8 Hz, 1H); 7.82 (d, J=8.4 Hz, 1H); 11.81 (bs, 1H).
95.8% at 0 - 110℃; for 16 h; Step 1 : To a solution of 2-amino-4-bromobenzoic acid (4 g, 18.51 mmol) in 1,4-dioxane (40 mL) was added bis(trichloromethyl)carbonate in 1,4-dioxane (1.81 g, 6.11 mmol) drop wise at 0 °C. The reaction mixture was stirred at 110 °C for 16 h. The solvent was evaporated under reduced pressure and washed with n-hexane to afford 7-bromo-lH- benzo[d][l,3]oxazine-2,4-dione (4.3 g, 95.8percent LC-MS 97percent).]H NMR: (400 MHz, DMSO- d6) S (ppm) 11.8 (s, 1H), 7.80 (d, J= 8.4 Hz, 1H), 7.40 (d, J= 8.4 Hz, 2H); MS (ESI) m/z 243.02 [C8H4BrN03+H]+.
95.8% at 0 - 110℃; for 16 h; To a solution of 2-amino-4-bromobenzoic acid (4 g, 18.51 mmol) in 1,4-dioxane (40 mL) was added bis(trichloromethyl)carbonate in 1,4-dioxane (1.81 g, 6.11 mmol) drop wise at 0° C.
The reaction mixture was stirred at 110° C. for 16 h.
The solvent was evaporated under reduced pressure and washed with n-hexane to afford 7-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (4.3 g, 95.8percent LC-MS 97percent).
H NMR: (400 MHz, DMSO-d6) δ (ppm) 11.8 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.40 (d, J=8.4 Hz, 2H); MS (ESI) m/z 243.02 [C8H4BrNO3+H]+.
89% at 70℃; for 12 h; General procedure: A 500 mL single neck round-bottomed flask equipped with a football-shaped PTFE stirring bar (16 mm × 37 mm) was chargedwith 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol,1.0 equiv) followed by the addition of tetrahydrofuran (230 mL,0.2 molar) and solid triphosgene (13.7 g, 46.3 mmol, 1.0 equiv)resulting in a suspension. The reaction vessel was placed into afitted metal heating mantle and the neck was equipped with a24/40 Liebig condenser. The suspension was stirred (500 rpm)and the heating mantle set to 70 °C. The suspension becamehomogenous before a white solid precipitated out after about30 minutes at 70 °C. The heterogeneous reaction mixture wasaged for 12 hours then cooled to room temperature (25 °C). Theslurry was poured into a 600 mL beaker equipped with overheadmechanical stirrer (PTFE 75 mm paddle) containing250 mL of deionized water. With vigorous stirring, the mixturebecame homogenous followed by precipitation of a pale whitesolid. The solid was collected by vacuum filtration on aBüchner funnel (7.6 cm diameter) with Whatman 1 filter paper(70 mm) and air pulled through for 5 minutes. The material was transferred to a 250 mL Erlenmeyer flask equipped with cylindricalstir bar and 50 mL of methanol was added. The slurrywas stirred for 10 minutes and then collected by vacuum filtration.The filter cake was dried under vacuum (0.1 mmHg at 25 °C) for 12 hours to afford 9b as a white powder (90percent yield).
68% at 80℃; Inert atmosphere The 2-amino-4-bromobenzoic acid (10.0g, 46 . 3mmol) dissolved in tetrahydrofuran (100 ml) in, adding triphosgene (4.54g, 15 . 3mmol), under the protection of nitrogen is heated to 80 °C stirring overnight. Cooling to room temperature, the reaction solution the ice water (120 ml) in, filtering, the filter cake are sequentially water, ether washing, drying, to obtain brown solid (7.60g, 68.0percent).

Reference: [1] Patent: US2011/251194, 2011, A1, . Location in patent: Page/Page column 17
[2] Patent: WO2013/147711, 2013, A1, . Location in patent: Page/Page column 158
[3] Patent: US2014/371199, 2014, A1, . Location in patent: Paragraph 0584
[4] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2529 - 2536
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6928 - 6937
[6] Patent: CN105384687, 2016, A, . Location in patent: Paragraph 0268; 0269; 0271; 0272; 0273
[7] Patent: WO2011/75699, 2011, A2, . Location in patent: Page/Page column 104
[8] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[9] Patent: EP3357916, 2018, A1, . Location in patent: Paragraph 0085
  • 7
  • [ 75-44-5 ]
  • [ 20776-50-5 ]
  • [ 76561-16-5 ]
Reference: [1] Patent: WO2008/130600, 2008, A2, . Location in patent: Page/Page column 55
  • 8
  • [ 67-56-1 ]
  • [ 20776-50-5 ]
  • [ 135484-83-2 ]
YieldReaction ConditionsOperation in experiment
86% for 24 h; Reflux A single-mouth bottle was charged with 10 g of 2-amino-4-bromobenzoic acid, 150 ml of methanol, and 10 ml of concentrated sulfuric acid, and the mixture was heated under reflux for 24 hrs.It was cooled to room temperature and concentrated under reduced pressure to remove methanol.Add 100 ml of ethyl acetate, 100 ml of 5percent sodium carbonate solution, stir for 5 mins, and let stand for stratification.The aqueous layer was separated and the organic layer was washed with 100 ml of water.Dry over anhydrous sodium sulfate and concentrate under reduced pressureMethyl 2-amino-4-bromobenzoate 9.16 g, yield 86percent.
85%
Stage #1: at 20℃; for 24 h;
Stage #2: With sodium hydrogencarbonate In water
PREPARATION 37; 2-Amino-4-bromobenzoic acid methyl ester.2-Amino-4-bromobenzoic acid (Boojamra et al., Journal of Organic Chemistry (1997), 62(5), 1240-1256) (0.60 g, 2.78 mmol) in MeOH (20 mL) was saturated with HCI gas, allowed to cool back to rt and saturated again. The mixture was stirred 24hrs, concentrated and partitioned between EtOAc and sat. aq. NaHCO3. The organics were washed with brine, dried (MgSO4) and concentrated to yield 0.54 g (85percent) of PP37 as a waxy brown solid: NMR (CDCI3) 7.66 (d, J = 8.7 Hz, 1 H), 6.82 (d, J= 2.1 Hz, 1 H), 6.73 (dd, J= 8.7, 2.1 Hz, 1 H), 3.83 (s, 3H).
76.7% at 20 - 80℃; for 12 h; Cooling with ice 3.00 g (13.89 mmol) of 2-amino-4-bromobenzoic acid was placed in a 250 mL pressure-Then add 10mL of concentrated sulfuric acid under ice-cooling, stir for 5min at room temperature, then seal and heat 12KTLC at 80 ° C. After the reaction is complete, cool to room temperature.The reaction mixture was poured into an ice-water mixture. Sodium bicarbonate was slowly added to the reaction mixture until no more bubbles were formed, and then extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, Petroleum ether: ethyl acetate = 15: 1, 200 mesh silica gel column chromatography, 2-amino-4-bromobenzoic acid methyl ester 2.45g, yield 76.7percent
Reference: [1] Patent: CN107778229, 2018, A, . Location in patent: Paragraph 0026
[2] Patent: WO2006/48727, 2006, A1, . Location in patent: Page/Page column 77
[3] Patent: CN103554007, 2016, B, . Location in patent: Paragraph 0044; 0052; 0053
[4] British Journal of Pharmacology, 2018, vol. 175, # 12, p. 2504 - 2519
[5] Journal of the Chemical Society, 1931, p. 72,73
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[7] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925
  • 9
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  • [ 20776-50-5 ]
YieldReaction ConditionsOperation in experiment
96% With iron(III) chloride; sodium hydroxide; hydrazine In water; isopropyl alcohol at 75℃; for 2 h; 2)
To 4-bromo-2-nitrobenzoic acid (1.80 g, 7.83 mmol) were added 0.88N aqueous sodium hydroxide solution (10 ML), iron(III) chloride (133 mg) and isopropyl alcohol (0.7 ML) and the mixture heated to 75° C.
While stirring the mixture, hydrazine (1.1 ML) was slowly added, and the mixture was reacted at 75° C. for 2 hrs.The reaction mixture was filtered and the filtrate was concentrated.The precipitated solid was washed with water to give 4-bromoanthranilic acid (1.73 g, 96percent).
1H NMR (DMSO-d6) δ ppm: 6.62 (dd, J=1.5, 8.5 Hz, 1H), 6.95 (d, J=1.5 Hz, 1H), 7.56 (d, J=8.5 Hz, 1H).
58% With hydrogen In tetrahydrofuran; ethanol for 66.5 h; EXAMPLE 14 7-(3-Amino-propyl)-3H-quinazolin-4-one14A. 2-Amino-4-bromo-benzoic acid; 4-Bromo-2-nitro-benzoic acid (0.5g, 2.03 mmol) (Matrix, 009241) was dissolved in a 1 : 1 mixture of ethanol/ tetrahydrofuran (22 ml). This solution was added to 5percent platinum on carbon (0.2g, 50percent water content) under an atmosphere of nitrogen. The reaction was shaken under an atmosphere of hydrogen for 2.5 hours. A further batch of platinum on carbon was added (0.2g) and the mixture was shaken for 64 hours under an atmosphere of hydrogen. The reaction mixture was filtered, washing through with a 1 : 1 mixture of ethanol/ tetrahydrofuran. The solvent was removed under reduced pressure and the residue was purified by flash silica chromatography, eluting with methanol/ dichloromethane (2:98) to yield the title compound as a yellow solid (0.253g, 58percent). LC/MS: (PS-Al) R12.62 [M+H]+ 215.88.
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 31
[2] Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223
[3] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1240 - 1256
[4] Patent: WO2006/51290, 2006, A2, . Location in patent: Page/Page column 111; 144
[5] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[6] Chemische Berichte, 1912, vol. 45, p. 2078
[7] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 204
[8] Journal of the American Chemical Society, 1960, vol. 82, p. 5918 - 5923
[9] Patent: US2004/167128, 2004, A1, . Location in patent: Page 38
[10] Patent: WO2004/18419, 2004, A2, . Location in patent: Page 321
  • 10
  • [ 6326-79-0 ]
  • [ 20776-50-5 ]
YieldReaction ConditionsOperation in experiment
83.7%
Stage #1: at 20℃; for 0.5 h;
Stage #2: at 20℃; for 1 h; Cooling with ice
20 mL of 5percent NaH was taken into a 100 mL round bottom flask,Then slowly add 4.0ml 6-bromoindole dione, stirring at room temperature for 30min,8 mL of H2O2 solution was added under ice-cooling,Remove the ice room temperature reaction lh JLC detection reaction is complete,The precipitate was collected by filtration and dried in vacuo to give 3.20 g of 2-amino-4-bromobenzoic acid in a yield of 83.7percent.
21%
Stage #1: With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 2 h;
Stage #2: With hydrogenchloride In water at 0℃;
Step 3: 2-Amino-4-bromo-benzoic acidTo a 500 mL round bottom flask, 6-bromo-lH-indole-2,3-dione (50 g, 0.2192 mol) and NaOH (20 g in 250 mL water) were added and cooled the reaction vessel to 0 °C. To this reaction mixture 30percent> hydrogen peroxide (50 mL) was slowly added. The reaction mixture was stirred at 0 °C for 2 h. Subsequently, the reaction mixture was acidified with 2N HC1 [pH-6] at 0 °C to afford the solid compound. The solid material was collected by filtration and dried to obtain the title compound [10 g, 21percent]. 1H NMR (300 MHz, DMSO-de): δ 7.59 (d, J = 8.7 Hz, 1H), 6.96 (d, J = 2.1 Hz, 1H), 6.65 (dd, J = 8.7 Hz, J" = 1.8 Hz, 1H)
10 g With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 2 h; To a 500 mL round bottom flask, 6-bromo-1H-indole-2,3-dione (50 g, 0.2192 mol) and NaOH (20 g in 250 mL water) were added and the reaction vessel was cooled to 0° C. To this reaction mixture, 30percent hydrogen peroxide (50 mL) was slowly added. The reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was then acidified with 2N HCl (pH 6) at 0° C. to afford the solid compound. The solid material was collected by filtration and dried to obtain the title compound (10 g, 21percent). 1H NMR (300 MHz, DMSO-d6): δ 7.59 (d, J=8.7 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H), 6.65 (dd, f=8.7 Hz, f′=1.8 Hz, 1H) LC-MS (ESI): Calculated mass: 215.0; Observed mass [M+H]+: 217.9. (RT: 0.83 min).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6293 - 6297
[2] Patent: CN103554007, 2016, B, . Location in patent: Paragraph 0044; 0050; 0051
[3] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 91-92
[4] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[5] Patent: US2014/38952, 2014, A1, . Location in patent: Page/Page column 0156-0157
[6] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834
  • 11
  • [ 117323-99-6 ]
  • [ 20776-50-5 ]
YieldReaction ConditionsOperation in experiment
98.3%
Stage #1: at 25℃; for 12 h;
Stage #2: With hydrogenchloride In ethanol; water
Method 3; 2-Amino-4-bromobenzoic acid; A solution of 2-amino-4-bromobenzoic acid ethyl ester (6 g, 24.5 mmol) in 84 ml of ethanol was treated with sodium hydroxide (1.97 g in 17 ml water). The reaction mixture was stirred at 25 °C for 12 hours. The ethanol was removed by distillation and the resulting suspension was diluted with water (200 ml) and acidified with 10percent HCI to pH=1-3. The white solid was collected by filtration, washed with water and dried via high vacuum (5.2 g, 98.3percent).
Reference: [1] Patent: WO2005/123696, 2005, A1, . Location in patent: Page/Page column 66
  • 12
  • [ 135484-83-2 ]
  • [ 20776-50-5 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; ethanol at 50℃; for 3 h;
Stage #2: With hydrogenchloride In water
Compound 36 (10 g, 43.5 mmol) and NaOH (5.2 g, 130.4 mmol) were dissolved in H20 (40 mL), CH3CH2OH (40 mL) and THF (120 mL). The reaction mixture was stirred for 3 hours at 50°C. The organic solvent was then removed under vacuum. The residue was extracted with ethyl acetate (3 x 50 mL). The water layer was acidified with con. HCl until pH=2 and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were concentrated under vacuum to afford product 37 (9.3 g, 98percent yield).
Reference: [1] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 48
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Reference: [1] Patent: US2005/261307, 2005, A1,
  • 14
  • [ 19201-53-7 ]
  • [ 20776-50-5 ]
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2011, vol. 338, # 1-2, p. 92 - 104
  • 15
  • [ 60956-26-5 ]
  • [ 20776-50-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[2] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[3] Journal of the American Chemical Society, 1960, vol. 82, p. 5918 - 5923
  • 16
  • [ 106-38-7 ]
  • [ 20776-50-5 ]
Reference: [1] Journal of the American Chemical Society, 1960, vol. 82, p. 5918 - 5923
  • 17
  • [ 611-00-7 ]
  • [ 20776-50-5 ]
Reference: [1] Patent: US5744638, 1998, A,
  • 18
  • [ 6941-75-9 ]
  • [ 20776-50-5 ]
  • [ 5794-88-7 ]
Reference: [1] Molecules, 2010, vol. 15, # 8, p. 5561 - 5580
  • 19
  • [ 64945-30-8 ]
  • [ 20776-50-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 261 - 268
  • 20
  • [ 610-36-6 ]
  • [ 20776-50-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1240 - 1256
  • 21
  • [ 37125-92-1 ]
  • [ 20776-50-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 261 - 268
  • 22
  • [ 591-19-5 ]
  • [ 20776-50-5 ]
Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
[3] Patent: CN103554007, 2016, B,
  • 23
  • [ 65971-74-6 ]
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Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
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  • [ 20776-50-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1912, vol. 388, p. 34
[2] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
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  • [ 79603-03-5 ]
  • [ 20776-50-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 204
[2] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
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  • [ 116436-10-3 ]
  • [ 20776-50-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[2] Justus Liebigs Annalen der Chemie, 1912, vol. 388, p. 34
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 204
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  • [ 39478-78-9 ]
  • [ 20776-50-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
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  • [ 20776-50-5 ]
  • [ 917-54-4 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
33% at -78℃; for 1 h; To a -78 °C solution of 2-amino-4-bromobenzoic acid (2.16 g, 10 mmol) in THF (20 mL) was added MeLi (13.3 mL, 3M, 0.04 mmol). The resulting reaction was allowed to stir at -78 °C for 1 hour, then was quenched with water and extracted with EtOAc. The organic extract was dried over anhydrous Na2S04, filtered and concentrated in vacuo and the resulting residue was purified using flash chromatography on silica gel to provide Int-21 (700 mg, 33 percent). 1H NM (CDC13): δ 7.51 - 7.58 (m, 1 H), 6.72 - 6.84 (m, 2 H), 6.37 (s, 2 H), 7.73 (s, 2 H). MS (ESI) m/e (M+H*): 214.
Reference: [1] Patent: WO2012/50848, 2012, A1, . Location in patent: Page/Page column 121
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  • [ 91270-69-8 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 1, p. 155 - 166
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  • [ 91270-68-7 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 1, p. 155 - 166
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  • [ 98-80-6 ]
  • [ 4445-43-6 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16 h; Inert atmosphere 2. i. 3 -amino- [ 1, 1 '-biphenylj -4-carboxylic acid:
To a mixture of 2-amino-4-bromobenzoic acid (0.992 g; 4.46 mmol), phenylboronic acid (0.832 g; 6.69 mmol) and Pd(PPh3)4 (0.052 g; 0.045 mmol) under nitrogen was added degassed DMF (10 mL) and aq. \M K2C03 (7 mL). The resulting mixture was stirred at 80°C for 16 h. DMF was removed under reduced pressure. The residue was taken up in 4N NaOH (40 mL) and the aq. phase was washed twice with EA (2 x 50 mL). The pH of the aq. layer was adjusted to 5 by addition of 4N HC1. The aq. phase was extracted three times with EA (3 x 50 mL) and once with DCM-MeOH 9-1 (50 mL). The combined org. layers were dried over MgS04 and evaporated under reduced pressure to give a beige solid. It was triturated in Et20, filtered and dried to give the title compound as a beige solid (0.721 g; 76percent yield). MS (ESI, m/z): 214.3 [M+H+] for Ci3HnN02; tR = 0.78 min.
Reference: [1] Patent: WO2015/173329, 2015, A1, . Location in patent: Page/Page column 99
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Reference: [1] Patent: WO2008/154642, 2008, A2, . Location in patent: Page/Page column 182
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  • [ 112253-70-0 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: With ammonia In water; N,N-dimethyl-formamide at 20℃; for 15 h;
Compound 37 (9.3 g, 43.1 mmol), HOBT (13.4 g, 99 mmol) and EDC.HC1 (19 g, 99 mmol) were dissolved in DMF (40 mL). The solution was stirred at 20°C for 30 minutes. To the solution, H3.H2O (20 mL). was slowly added The reaction mixture was stirred for 15 hours at room temperature. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL). The mixture was washed with saturated NaHC03 and H4CI aqueous solution. The organic layer was dried over Na2S04 and concentrated under vacuum to give the compound 38 (6.2 g, 67percent yield).
53% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 25℃; for 18.5 h; Inert atmosphere To a solution of 2-amino-4-bromobenzoic acid (10g, 46.3 mmol) in tetrahydrofuran (THF) (10 mL) was added HOBT (16.30 g, 106 mmol) and EDC (20.41 g, 106 mmol). The mixture was stirred at 25 °C for 30 min when ammonia (30 mL, 1386 mmol) was added to the solution. The mixture was stirred at 25 °C for 18 hr. The solvent was removed in vacuo when EtOAc (200 mL) was added to the mixture. The organic phase was washed with NaHC03 (aq, 100 mL X 3) and dried with NaS204. The solvent was removed to afford 2-amino-4-bromobenzamide (5.5g, 24.55 mmol, 53 percent yield).
40% With ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 20℃; for 24 h; To a solution of 2-amino-4-bromobenzoic acid (1 equiv) in DMA (0.23 M), were added ammonium chloride (7 equiv), HBTU (1 equiv) and diisopropylethylamine (2 equiv). The reaction mixture was stirred for 24 hours at room temperature. DMA was evaporated and the residue was purified by flash column chromatography onto silica gel eluting with a gradient of TBME/hexane to yield the desired product as a white solid. 2-Amino-4-bromo-benzamide: 40 percent yield, 100 percent purity) m/z (LC-MS, ESP): 215 [M+H]+ R/T = 3.00 min
Reference: [1] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 48
[2] Patent: WO2017/98440, 2017, A1, . Location in patent: Page/Page column 120
[3] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 119
[4] Patent: WO2011/75699, 2011, A2, . Location in patent: Page/Page column 206
[5] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
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  • [ 573675-55-5 ]
Reference: [1] Patent: US2013/12489, 2013, A1,
[2] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[3] Patent: WO2009/111028, 2009, A1,
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  • [ 56-81-5 ]
  • [ 928839-62-7 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
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  • [ 946122-05-0 ]
Reference: [1] Angewandte Chemie, International Edition, 2014, vol. 53, # 36, p. 9603 - 9607,5[2] Angewandte Chemie, 2014, vol. 126, # 36, p. 9757 - 9761,5
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  • [ 60-35-5 ]
  • [ 20776-50-5 ]
  • [ 114703-12-7 ]
YieldReaction ConditionsOperation in experiment
90% at 195℃; for 3 h; Step 4: 7-Bromo-lH-quinazoline-2,4-dioneTo a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195 °C for 3 h. The reaction mixture was allowed to reach 80 °C and water was added. The aqueous reaction mixture was stirred at 80 °C for 5-10 min then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound [10 g, 90percent]. This material was taken to the next step without any further purification.
Reference: [1] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 92
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  • [ 20776-50-5 ]
  • [ 57-13-6 ]
  • [ 114703-12-7 ]
YieldReaction ConditionsOperation in experiment
10 g at 195℃; for 3 h; To a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195° C. for 3 hours. The reaction mixture was allowed to cool to 80° C. and water was added. The aqueous reaction mixture was stirred at 80° C. for 5-10 minutes then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound (10 g, 90percent). This material was taken to the next step without further purification.
Reference: [1] Patent: US2014/38952, 2014, A1, . Location in patent: Page/Page column 0158-0159
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  • [ 917-61-3 ]
  • [ 114703-12-7 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834
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  • [ 959237-68-4 ]
Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
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Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 45, p. 9680 - 9684
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