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Chemical Structure| 130049-82-0
Chemical Structure| 130049-82-0
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Product Details of [ 130049-82-0 ]

CAS No. :130049-82-0 MDL No. :MFCD09835552
Formula : C11H15ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JKVUGXRJSYRXFN-UHFFFAOYSA-N
M.W : 242.70 Pubchem ID :15547194
Synonyms :

Calculated chemistry of [ 130049-82-0 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.64
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.92
TPSA : 55.12 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) : -7.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 0.56
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 1.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.84
Solubility : 3.48 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (Ali) : -1.29
Solubility : 12.5 mg/ml ; 0.0513 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.337 mg/ml ; 0.00139 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.2

Safety of [ 130049-82-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 130049-82-0 ]

* 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 [ 130049-82-0 ]
  • Downstream synthetic route of [ 130049-82-0 ]

[ 130049-82-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 130049-79-5 ]
  • [ 130049-82-0 ]
YieldReaction ConditionsOperation in experiment
72.6%
Stage #1: With hydrogenchloride; hydrogen In methanol at 27℃; for 36 h; Inert atmosphere
Stage #2: With sodium hydroxide In water at 5℃;
At room temperature, 3-(2-chloroethyl)-2-methyl-9-benzyloxy-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one 4.0g (0.0122mole) was charged into a 250 mL three-necked bottle, 80 mL methanol was added, and then concentrated hydrochloric acid (about 25 drops) was added dropwise with stirring to adjust pH to 3.0.
After the dissolution was completed, 1.8g of wet 5percent Pd-C (water content: 56percent) (W/W: 10/1) was added, argon gas was fed to exchange atmosphere for three times, hydrogen gas was fed to exchange atmosphere for three times, the reaction was conducted at 27°C for about 36 hours, and TLC (ethyl ether: n-hexane: methanol: triethylamine = 2mL: 0.5mL: 6 drops:
6 drops) was used to detect the debenzylated product.
The reaction was stopped after all starting materials were consumed.
A light green liquid was obtained by sucking filtration, and distilled at a reduced pressure to remove solvent to obtain a dark green viscous liquid.
About 16mL distilled water was added, dissolution was conducted under ultrasound, the temperature was decreased to 5°C by using an icewater bath, and the pH was adjusted to 10-11 by adding 2N aqueous sodium hydroxide so as to precipitate a large amount of white solid when the pH was close to its end.
The white solid was filtered out at a reduced pressure.
The filtrate was extracted with 2x20mL of dichloromethane.
The organic layers were combined and washed with saturated aqueous NaCl solution for twice (10mL per time), dried over anhydrous magnesium sulfate.
Light yellow solids were obtained after the solvent was distilled out.
The resulting solids were combined and dried to obain 2.14g product (yield: 72.6percent). Mp: 100.8-102.7°C.
69% With hydrogenchloride; hydrogen In water at 25 - 30℃; for 4 - 6 h; Example (8):Preparation of 9-hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H- pyrido [l,2a|pyrimidin-4-one of Formula IITo a 500 mL hydrogenation flask 9-benzyloxy-3-(2-chloroethyl)-2-methyl-4H- pyrido[ l ,2-a]pyrimidin-4-one ( 10.0 gm), water ( 10O mL), Cone. HCI ( 12 ml_) and 10percent <n="16"/>Pd/C (2.0 gm of 50percent wet) were added and the contents were treated w ith hydrogen gas at pressure 1 -2 Kgs under agitation for 4 to 6 hrs at 25 to 3O0C. The catalyst was filtered and filtrate was concentrated under vacuum completely to get residue ( 10 gm). To the residue added water ( 100 mL) and adjusted the pH to 5 - 6 with potassium acetate solution (24 gm in 100 mL). The resulting crystal was flittered at 0 to 50C, washed with water and dried in vacuum to obtain 9-hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9- tetrahydro-4H-pyrido[ l ,2a]pyrimidin-4-one. (5.1 gm, theoretical yield 69 percent).
Reference: [1] Patent: EP2154138, 2010, A1, . Location in patent: Page/Page column 7
[2] Patent: WO2009/60297, 2009, A2, . Location in patent: Page/Page column 14-15
  • 2
  • [ 849727-62-4 ]
  • [ 130049-82-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With hydrogen In water; isopropyl alcohol at 55℃; Inert atmosphere
Stage #2: With potassium acetate In water
Example 4: 3-(2-chloroethyl)6,7,8,9-tetrhydro-2-methyl-9-hydroxy-4H- pyrido[l,2-a]pyrimidin-4-one, V2.75 g (10 mmol) of IX.HC1, 40 ml of IPA/H2O (19: 1 v/v, 0.25 M) and 404 mg of Pd/C catalyst (5percent w/w (dry), containing 66.20percent water) are placed in a reaction vessel and purged with nitrogen (~40 psi) five times at room temperature.Afterwards, the reaction vessel is purged an extra five times with hydrogen (50-60 psi) and heated up to 55°C under hydrogen (at atmospheric pressure) over 20 minutes. After that, the vessel is pressurized with hydrogen (15 psi) and mechanical stirring supplied (1500 rpm) at 55°C for 3 hours. The reaction vessel is then cooled to room temperature and carefully vented.Analysis of the supernatant by HPLC showed that high conversions are achieved, over 98 percent, and less than 1percent of the de-chlorinated by-product is produced.The reaction solution is filtered over celite, the filtered cake washed with MeOH and the combined filtrates evaporated to dryness to give V.HC1, as an off-white solid. A solution of potassium acetate in water is added drop wise, until complete <n="15"/>precipitation of compound V is achieved. The obtained precipitate is filtered and washed with water, yielding 2.23g (92percent yield) of compound V.Analytical data of V. HCl:RMN 1H (D2O) δ (ppm): 1.91-2.37 (m, CH2-CH2), 2.53 (s, CH3); 3.07 (t, CH2); 3.80(t, CH2Cl); 4.01 (at, CH2); 4.97 (t, CH-OH).Analytical data of V:RMN 1U (CDCl3) δ (ppm): 1.72-2.33 (m, CH2-CH2), 2.37 (s, CH3); 3.01 (t, CH2);3.77 (t, CH2Cl); 3.94 (at, CH2); 4.52 (t, CH-OH).
68.25%
Stage #1: at 50 - 55℃;
Stage #2: With hydrogen In methanol at 50 - 55℃; for 8 h;
Into a clean and dry 3L, four-necked RB flask equipped with shaft, condenser, gas passing tube and thermo socket was charged lOOg (0.363 moles) of (2-chloroethyl)-9- hydroxy-2-methyl-4H-pyrido[l,2-a]pyrimidin-4-one mono hydrochloride (formula- XI) and 2000ml of methanol. The reaction mass was slowly heated to 50-550C using a <n="16"/>water bath. After reaching 50-550C, 2Og of 10percent palladium-on-charcoal catalyst was charged and hydrogen gas was slowly bubbled into the reaction mass. Progress of the reaction was monitored by TLC and found to be over after 8h.Reaction mass was filtered of and the filtrate is evaporated at 60-65°C on a rotavapor under vacuum to get yellow colored syrup. The syrup was dissolved in 370ml of water at 80-820C and cooled to 25-35°C. Aqueous potassium acetate (prepared from 71.28 g of potassium acetate and 70ml of water) was added to the reaction mass. The resulting suspension was cooled to 5-100C, stirred for 2h and filtered under suction, washed with 200ml of water to get 92g of wet solid.The above wet solid was recrystallized from methanol to yield 60.2Og (yield 68.25percent) the title compound. Melting point: 102-1050C. Purity by HPLC is >97percent. 1H-NMR (CDCl3): 1.8 (m, IH, aliphatic-H), 1.96 (m, IH, aliphatic-H), 2.16 (m, IH, aliphatic- H)5 2.37 (m, 4H, aliphatic-H), 3.0 (m, 2H aliphatic-H,), 3.75 (t, 2H, -CH2-, J= 6.84 Hz), 3.97 (m, 2H5 aliphatic-H), 4.17 (s, IH5 -OH5 D2O exchangeable), and 4.50 (m, IH, aliphatic-H).
39%
Stage #1: With pyrographite In methanol at 50 - 55℃; for 0.75 h; Large scale
Stage #2: With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane at 25 - 30℃; Large scale
A suspension of methanol (560 L) and 3a (70 Kg, 255.31 mole) in a1 KL SS reactor was heated to 50–55 °C to achieve dissolution. Charcoal (1.5 Kg) was then added to the solution and heating was continued at 50–55 °C for 45 min. The contents were filtered and the charcoal cake was washed with methanol (70 L). The combined filtrate, the catalyst (10percent Pd/C, 50percent wet, 15.4 Kg) and dichloromethane (140 L)were added to a 1 KL hydrogenation reactor and the mixture was hydrogenated at pressureof 42–57 psi at 25–30 °C for 3–4 h. The hydrogen pressure was then reduced to 28–43 psi until completion of reaction by HPLC. Then the catalyst was filtered off and the catalyst was washed with methanol (70 L). The combined filtrate was evaporated at temperature below 50 °C under reduced pressure to give a dark grayish oil. Purified water(350 L) was added to the oil and pH of the resulting solution was adjusted to 7.3–7.5 using aqueous ammonia at 10–15 °C. The precipitated product was collected and washed with purified water (35 L). The wet product was dissolved in dichloromethane (175 L)and the solution was washed with aqueous sodium hydroxide (0.875 kg NaOH dissolvedin 52 L water) followed by purified water (52 L x 2) and then with the brine (7 kg NaCl dissolved in 52 L water) at 0 – 5 °C. Finally the dichloromethane layer was decolorized using activated charcoal (1.5 Kg) and then evaporated below 40 °C under reduced pressure to afford a gray colored solid. The residue was dissolved in ethanol (70 L) at 70–75 °C and the solution was gradually cooled to 10–15 °C to give a precipitate which was stirred for an additional 1 h. The precipitated product was collected, washed with t-butylmethyl ether (9 L) and dried at 40–45 °C under reduced pressure to provide 24 kg (39percent)of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (4a), mp. 107–108 °C (lit.14. 100–102 °C), HPLC (w/w percent): 4a (99.47percent), unknown impurity (0.05percent) and compound 5 (0.48percent) (total impurity 0.53percent). Compounds 1a, 2, 3a,3b, 4b and 6 were not detected by HPLC chromatography. UV (MeOH) λmax (e): 280 nm,233 nm. MS (ESI, m/z): 243 [M + H]C; FT-IR (KBr): 3145, 1664.2, 1326.7,1183.89 cm1; 1H NMR (CDCl3): d 1.76–1.80 (m, 1H), 1.89–2.00 (m, 1H), 2.08–2.15(m, 1H), 2.31–2.38 (m, 4H), 2.95–3.03 (m, 2H), 3.73–3.76 (t, 2H, J 6.80 Hz, -CH2-N),3.85–3.98 (m, 2H,-CH2-Cl), 4.09–4.09 (d, 1H, J 1.2 Hz, O-H), 4.46–4.50 (m,1H, CH-OH); 13C NMR (CDCl3): d 18.04, 21.30, 26.91, 29.85, 42.38, 42.54, 66.74, 118.32,157.97, 159.11, 161.59
Reference: [1] Patent: WO2009/144288, 2009, A1, . Location in patent: Page/Page column 13-14
[2] Patent: WO2009/10988, 2009, A1, . Location in patent: Page/Page column 14-15
[3] Organic Preparations and Procedures International, 2016, vol. 48, # 3, p. 296 - 302
[4] Patent: US2009/182150, 2009, A1, . Location in patent: Page/Page column 3-4
[5] Patent: WO2011/73997, 2011, A2, . Location in patent: Page/Page column 15
[6] Patent: US2011/293889, 2011, A1,
[7] Patent: WO2012/42368, 2012, A1, . Location in patent: Page/Page column 11
  • 3
  • [ 147687-17-0 ]
  • [ 130049-82-0 ]
YieldReaction ConditionsOperation in experiment
74.4% With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water; <i>tert</i>-butyl alcohol at 25 - 30℃; for 16 h; 25 ~ 30 ° C, 20L hydrogenation reactor were successively added 3L methanol, 3L tert-butanol, 300mL concentrated hydrochloric acid, 600g 9- (benzyloxy) -3- (2- chloroethyl) -2- Methyl-4H-pyrido [1,2-a] pyrimidin-4-one, dissolved with stirring,To the reaction vessel was added 120g of 10percent dry palladium on charcoal, replaced three times, and replaced with hydrogen three times.Control hydrogen pressure range 15psi, the reaction 16 hours Sample detection to detect the reaction solution 9- (benzyloxy) -3- (2-chloroethyl) -2-methyl-4H-pyrido[1,2-a] pyrimidin-4-oneOf the debenzymal product is less than 0.5percent (area normalization method) and then stop the reaction.The catalyst was removed by filtration and the methanol was distilled off under reduced pressure to give a yellow viscous material. Adding 900mL of purified water and 1800mL of dichloromethane, stirring to dissolve, cooling to 0 ~ 5 ° C, 20percent aqueous NaOH was added dropwise to adjust the pH to 8.00, standing still, the aqueous phase was extracted with 1800mLx2 dichloromethane, the combined organic phase, Drying over anhydrous sodium sulfate.The filtrate was concentrated to give a dark green solid residue was added to the concentrated residue 3600mL ethyl acetate, heated to reflux to clear, add 120g kaolin stirring decolorization 30 minutes, filtered, to the filtrate was added 7200ml of petroleum ether, cooled to 0 ~ 5 ° C,Stirring crystallization 2 hours, filtered, the filter cake in a blast oven, 50 ~ 55 ° C dried to constant weight of the discharge, the key intermediates, white-like solid powder,329.75 g of 3- (2-chloroethyl) -9-hydroxy-2-methyl-6,7,8,9-tetrahydro-411-pyrido [1,2-a]Molar yield 74.4percent.Purity: 99.30percent, chlorine out of the compound V: Ν.
69% With hydrogenchloride; hydrogen In water at 25 - 30℃; Example (8)
Preparation of 9-hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2a]pyrimidin-4-one of Formula II To a 500 mL hydrogenation flask 9-benzyloxy-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (10.0 gm), water (100 mL), Conc. HCl (12 mL) and 10percent Pd/C (2.0 gm of 50percent wet) were added and the contents were treated with hydrogen gas at pressure 1-2 Kgs under agitation for 4 to 6 hrs at 25 to 30° C. The catalyst was filtered and filtrate was concentrated under vacuum completely to get residue (10 gm). To the residue added water (100 mL) and adjusted the pH to 5-6 with potassium acetate solution (24 gm in 100 mL). The resulting crystal was flittered at 0 to 5° C., washed with water and dried in vacuum to obtain 9-hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2a]pyrimidin-4-one. (5.1 gm, theoretical yield 69percent).
Reference: [1] Patent: CN107311998, 2017, A, . Location in patent: Paragraph 0041-0051; 0052-0053; 0054-0058
[2] Patent: US2010/298566, 2010, A1, . Location in patent: Page/Page column 6
[3] Patent: WO2009/45489, 2009, A2, . Location in patent: Page/Page column 6
[4] Patent: WO2009/45489, 2009, A2, . Location in patent: Page/Page column 7
[5] Patent: WO2009/44413, 2009, A2, . Location in patent: Page/Page column 6; 12
[6] Patent: WO2009/130710, 2009, A2, . Location in patent: Page/Page column 14
[7] Patent: US2010/298565, 2010, A1, . Location in patent: Page/Page column 14
[8] Patent: WO2011/15936, 2011, A2, . Location in patent: Page/Page column 11
[9] Patent: US8481729, 2013, B2,
  • 4
  • [ 1204248-71-4 ]
  • [ 130049-82-0 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: at 70℃; for 0.5 h; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In water
Example 2; Compound (1a); 0.50 g of the compound (6a) was suspended in 9.8 ml of 1M HCl under nitrogen and 8.4 ml of titanium (III) chloride were added. The solution was heated at 70° C. for 30 minutes. The reaction mixture was diluted with 20 ml of water and the solution was alkalized with sodium bicarbonate. The suspension was extracted with 4*25 ml of DCM. The organic solution was dried with sodium sulphate and evaporated. Yield: 0.41 g (87percent of theoretical yield), purity 96.8percent.
Reference: [1] Patent: US2010/10218, 2010, A1, . Location in patent: Page/Page column 11
  • 5
  • [ 260273-82-3 ]
  • [ 130049-82-0 ]
YieldReaction ConditionsOperation in experiment
99.32%
Stage #1: With hydrogenchloride; palladium 10% on activated carbon In ethanol; waterGreen chemistry
Stage #2: With hydrogen In ethanol; water at 80℃; Green chemistry
1) 200 g of 3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-A]pyrimidin-4-one was added to paliperidone hydrogenation precursor. 4L of anhydrous ethanol, 200g of concentrated hydrochloric acid, stirring evenly after adding 5g of 10percent Pd / C, fully stirred to form the material I; 2) Transfer the preheated material I and hydrogen from step 1) to the reaction module group of the microchannel reactor. The reaction was carried out, wherein: the flow rate of the slurry pump was adjusted so that the flow rate of the material I was 40.0 g/min, the flow rate of the H2 gas flow meter was adjusted to 700 ml/min, the reaction temperature was 80°C, the temperature of the cooling module was 25°C, and the reaction pressure At 1.5 MPa, the molar ratio of 3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-A]pyrimidin-4-one to H2 is 1:3.2. The total reaction time in the reaction module group was 20s; the reaction solution from the cooling module was collected, the catalyst was recovered by filtration, and the solvent was distilled off under reduced pressure. The residue was completely dissolved by adding 500 ml of water. The pH of the saturated NaHCO3 solution was 7 ~8, filtration, add 1.2L of ethyl acetate to the crude product, warm up to 60°C to dissolve, and slowly add 1.2L of n-hexane dropwise to it, add dropwise, cool to 010°C, keep stirring for 1h, filter, filter cake Wash with a small amount of n-hexane and vacuum dry at 50°C for 8 hours to obtain paliperidone intermediate 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl- 4H-pyrido[1,2-a]pyrimidin-4-one 128.91 g, yield 87.32percent, purity 99.28percent. In order to investigate the recycling efficiency of the catalysts, Pd/C and Pt/C were selected as catalysts. A total of 7 experiments were applied to the cycle. Among them, the amount of catalyst used in each reaction and other key process parameters were the same, and the cycle was examined. The relationship between the catalyst and the reaction conversion rate was applied several times. The results are shown in Tables 1 and 2:
Reference: [1] Patent: CN108003154, 2018, A, . Location in patent: Page/Page column 7-11
[2] Patent: WO2009/116071, 2009, A2, . Location in patent: Page/Page column 11-12
[3] Patent: WO2012/134445, 2012, A1, . Location in patent: Page/Page column 27-29
  • 6
  • [ 1254173-48-2 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2010/4578, 2010, A2, . Location in patent: Page/Page column 10; 19
  • 7
  • [ 1228559-69-0 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2010/64134, 2010, A2, . Location in patent: Page/Page column 7
  • 8
  • [ 147687-17-0 ]
  • [ 130049-82-0 ]
  • [ 260273-82-3 ]
YieldReaction ConditionsOperation in experiment
28.8 %Chromat. With hydrogenchloride; hydrogen In methanol; water at 25 - 30℃; for 1 h; Autoclave PREPARATION OF 3-(2-CHLOROETHYL)-9-HYDROXY-6, 7, 8.9-TETRAHYDRO-2- METHYL-4H-PYRIDO[l,2-a]PYRIMIDINE-4-ONE (FORMULA II)To a mixture of 3-(2-Chloroethyl)-9-benzyloxy-2-methyl-4H-pyrido[l,2- a]pyrimidine-4-one (35 g) and methanol (525 ml) added 34percent w/w aqueous hydrochloric acid (~8ml) to get a clear solution. This solution is hydrogenated in an autoclave in the <n="19"/>presence of palladium on charcoal (17.5 g) with 1.5-2 kg /cm2 of hydrogen pressure at 25- 300C. The progress of the reaction monitored by HPLC analysis at regular intervals and the results are given below.
Reference: [1] Patent: WO2009/130710, 2009, A2, . Location in patent: Page/Page column 17-18
  • 9
  • [ 147687-17-0 ]
  • [ 130049-82-0 ]
  • [ 849903-79-3 ]
YieldReaction ConditionsOperation in experiment
48.9 %Chromat. With hydrogenchloride; hydrogen In methanol; water at 25 - 30℃; for 3.5 h; Autoclave PREPARATION OF 3-(2-CHLOROETHYL)-9-HYDROXY-6, 7, 8.9-TETRAHYDRO-2- METHYL-4H-PYRIDO[l,2-a]PYRIMIDINE-4-ONE (FORMULA II)To a mixture of 3-(2-Chloroethyl)-9-benzyloxy-2-methyl-4H-pyrido[l,2- a]pyrimidine-4-one (35 g) and methanol (525 ml) added 34percent w/w aqueous hydrochloric acid (~8ml) to get a clear solution. This solution is hydrogenated in an autoclave in the <n="19"/>presence of palladium on charcoal (17.5 g) with 1.5-2 kg /cm2 of hydrogen pressure at 25- 300C. The progress of the reaction monitored by HPLC analysis at regular intervals and the results are given below.
Reference: [1] Patent: WO2009/130710, 2009, A2, . Location in patent: Page/Page column 17-18
  • 10
  • [ 1117803-76-5 ]
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Reference: [1] Patent: US2009/48272, 2009, A1,
  • 11
  • [ 517-23-7 ]
  • [ 24016-03-3 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: US2011/293889, 2011, A1,
  • 12
  • [ 517-23-7 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2011/73997, 2011, A2,
[2] Patent: WO2012/42368, 2012, A1,
[3] Patent: WO2012/134445, 2012, A1,
[4] Patent: US8481729, 2013, B2,
[5] Organic Preparations and Procedures International, 2016, vol. 48, # 3, p. 296 - 302
  • 13
  • [ 16867-03-1 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2011/73997, 2011, A2,
[2] Patent: WO2012/42368, 2012, A1,
[3] Organic Preparations and Procedures International, 2016, vol. 48, # 3, p. 296 - 302
[4] Patent: CN107311998, 2017, A,
  • 14
  • [ 24016-03-3 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2012/134445, 2012, A1,
[2] Patent: US8481729, 2013, B2,
[3] Patent: CN107311998, 2017, A,
  • 15
  • [ 181525-38-2 ]
  • [ 130049-82-0 ]
Reference: [1] Patent: WO2011/73997, 2011, A2,
[2] Patent: WO2012/42368, 2012, A1,
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Alcohols

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Related Parent Nucleus of
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Other Aromatic Heterocycles

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