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Chemical Structure| 73027-79-9
Chemical Structure| 73027-79-9
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Product Details of [ 73027-79-9 ]

CAS No. :73027-79-9 MDL No. :MFCD00234146
Formula : C6H3Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ILMIEWNDXAKVNI-UHFFFAOYSA-N
M.W : 192.00 Pubchem ID :817158
Synonyms :

Calculated chemistry of [ 73027-79-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.22
TPSA : 50.19 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) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.472 mg/ml ; 0.00246 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.43 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.63
Solubility : 0.446 mg/ml ; 0.00232 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 73027-79-9 ]

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 [ 73027-79-9 ]

* 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 [ 73027-79-9 ]
  • Downstream synthetic route of [ 73027-79-9 ]

[ 73027-79-9 ] Synthesis Path-Upstream   1~27

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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[2] Patent: WO2015/103355, 2015, A1,
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 4
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  • [ 166526-03-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[2] Patent: US2015/291629, 2015, A1,
  • 5
  • [ 40296-46-6 ]
  • [ 73027-79-9 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With sodium hydroxide; water In tetrahydrofuran; methanol for 0.5 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water
Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF:MeOH:water (600 mL). After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc:Et2O and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96percent).
96% With sodium hydroxide In tetrahydrofuran; methanol; water; toluene Step B:
Preparation of 4,6-dichloronicotinic acid (23): Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF/MeOH/water (600 mL).
After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc/Et2O and washed with water and brine.
The organic layer was dried (Na2SO4) and concentrated.
The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96percent).
96.3% With water; lithium hydroxide In tetrahydrofuran at 20℃; for 1 h; Scheme 30 compound 1 and LiOH were dissolved in THF/H20, the reaction mixture was stirred at RT for lh, cone HCl was added until PH= 5-6, The resulting mixture was stirred for 30 min at RT, some light red solid precipitated, the mixture was filtered and filter cake was washed with (DCM/MeOH = 2: 1) to give the scheme 30 compound 2 (4.2 g, yield 96.3percent) as a red solid.
83% With water; lithium hydroxide In tetrahydrofuran; ethanol at 25℃; for 2 h; Intermediate 521A: 4,6-Dichloronicotinic acid [0610] ethyl 4,6-dichloronicotinate (8 g, 36.4 mmol) in THF (50 mL), ethanol (25 mL) and water (25 mL) was added LiOH (2.61 g, 109 mmol). The mixture was stirred at 25° C. for 2 hours. The reaction mixture was concentrated to remove solvent. The residue was dissolved in water and acidified to neutral pH with 1.5 N HCl. The precipitated solid was filtered and washed with water (2×30 mL). The solid was dried to afford 4,6-dichloronicotinic acid (6.5 g, 83percent yield). LCMS 194.1 (M+2); 1H NMR (400 MHz, DMSO-d6) δ 8.80 (s, 1H), 7.93 (s, 1H).
83% With water; lithium hydroxide In tetrahydrofuran; ethanol at 25℃; for 2 h; To a solution of ethyl 4,6-dichloronicotinate (8 g, 36.4 mmol) in THF (50 mL), ethanol (25 mL) and water (25 mL) was added LiOH (2.61 g, 109 mmol). The mixture was stirred at 25 °C for 2 hours. The reaction mixture was concentrated in vacuo. Theresidue was dissolved in water and acidified to neutral pH with 1.5 N HC1. The precipitated solid was filtered and washed with water (2 x 30 mL). The solid was dried under vacuum to afford 4,6-dichloronicotinic acid (6.5 g, 83percent yield). LCMS m/z 194.1 (M+2); ‘H NMR (400 MHz, DMSO-d6) 8.80 (s, 1H), 7.93 (s, 1H).
70%
Stage #1: With water In 1,4-dioxane at 20℃;
Stage #2: With hydrogenchloride In 1,4-dioxane; water
Dichloropyridine X.1 (prepared using the procedure described in Brunette, S. R.; Kim, J. M.; Lemieux, R. M.; Aaron, M. US2006/0217417.) (164 mmol based on the theoretical yield of the previous step) was diluted with 100 mL of 1,4-dioxane followed by 1 M LiOH (197 mL, 197 mmol). The resulting cloudy solution was then stirred at rt until all starting material was consumed. The crude mixture was then acidified to pH=2 with 6 M HCl, then diluted with water until ppt formation ceased. The solids were then isolated by filtration affording the desired product as a light beige powder (22.14 g, 70percent). MS found for C6H3Cl2NO2 as (M+H)+ 192.0, 194.0. UV: λ=207, 273 nm.
4.79 g With sodium hydroxide In tetrahydrofuran; methanol; water at 20 - 25℃; for 0.5 h; (1) 2,4-dichloro-nicotinic acid ethyl (6.0g), It was added 1N aqueous sodium hydroxide solution (41 mL) in a mixture of methanol (5 mL) and THF (5mL). After stirring for 30 minutes at 20-25 , it was pH4 by the addition of 1 N hydrochloric acid. The precipitated crystals were collected by filtration, washed with water to give 4.79g of the dried 4,6-dichloro-pyridine-3-carboxylic acid

Reference: [1] Patent: US2005/49419, 2005, A1, . Location in patent: Page/Page column 24
[2] Patent: US2005/54701, 2005, A1,
[3] Tetrahedron Letters, 2011, vol. 52, # 4, p. 512 - 514
[4] Patent: WO2014/52365, 2014, A1, . Location in patent: Page/Page column 229-230
[5] Patent: US2015/191464, 2015, A1, . Location in patent: Paragraph 0611
[6] Patent: WO2016/210036, 2016, A1, . Location in patent: Page/Page column 62; 63
[7] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 8, p. 4442 - 4452
[8] Patent: US2012/108566, 2012, A1, . Location in patent: Page/Page column 55
[9] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[10] Patent: WO2014/74675, 2014, A1, . Location in patent: Paragraph 00185; 00196
[11] Patent: WO2014/74657, 2014, A1, . Location in patent: Paragraph 00146
[12] Patent: JP2015/124211, 2015, A, . Location in patent: Paragraph 0167
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YieldReaction ConditionsOperation in experiment
81%
Stage #1: With lithium hydroxide; water In tetrahydrofuran for 18 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃;
4,6-Dichloro-nicotinic acid methyl ester (27.3 g, 133 mmol) was dissolved in THF (150 mL). LiOH (3.53 g, 147 mmol), dissolved in H2O (25 mL), was added dropwise and the reaction was allowed to stir for 18 h.
The volatiles were removed in vacuo.
The resultant residue was diluted with H2O (100 mL) and acidified with 6 N HCl while swirling at 0° C.
The solution was brought to a pH of 2.0 and a yellow precipitate formed.
The mixture was allowed to stand at 0° C. for 1 h then filtered to afford 4,6-dichloro-nicotinic acid as a yellow solid (20.6, 81percent).
69%
Stage #1: With sodium hydroxide; water In tetrahydrofuran; methanol at 20℃; for 0.666667 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water
[00217] Step B; 4.6-Dichloronicotinic acid:[00218] To a solution of methyl 4,6-dichloronicotinate in a mixture of THF (400 ml), MeOH ( 100 ml) andH2O ( 100 ml) was added a solution of NaOH (10 g) in 40 ml H2O. The mixture was stirred for 40 min. at room temp. Then, the solvents were reduced and it was acidified with cone. HCl to a pH of about 2. It was extracted using a mixture of Et2O/EtOAc and the organic layer was dried with Na2SO4. The solvents were removed and the residue dried in vacuo to obtain the title compound as a white solid (12.3 g, 69percent). Rf (CHCl3/MeOH 10:1) = 0.85. 1H-NMR (300 MHz, DMSO-D6): δ = 8.80 (s, 1H), 7.90 (s, 1H).
3.2 g With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 1.5 h; To a stirred solution of methyl 4,6-dichloropyridine-3-carboxylate (3.5 g, 16.990 mmol) in THF (30 mL) was added a solution of lithium hydroxide monohydrate (3.56 g, 84.951 mmol) in water (15 mL). The reaction mixture was stirred at RT for 1.5 h. The progress of reaction was monitored by TLC. After completion of reaction, the pH of the aqueous layer was adjusted to 2 by the addition of 2 N HC1 (aq.) and the product was extracted with EtOAc (2x50 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 4,6- dichloropyridine-3-carboxylic acid (3.2 g) as a white solid.
2.60 g With lithium hydroxide monohydrate; water In tetrahydrofuran at 10 - 35℃; for 1 h; Lithium hydroxide monohydrate (665 mg) was added to a solution of methyl 4,6-dichloronicotinate (2.97 g) in THF (60 mL) and water (15 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. To the reaction solution was added 6N hydrochloric acid at room temperature, and the solvent was evaporated under reduced pressure. The residual solid was washed with water to give a white solid. The filtrate was extracted with ethyl acetate. The extract was washed with water and saturated brine, combined with an ethyl acetate solution of the solid obtained earlier, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.60 g) as a pale-yellow solid. (1378) 1H NMR (400 MHz, DMSO-d6) δ 7.94 (1H, s), 8.81 (1H, s), 13.63-14.30 (1H, m).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5648 - 5652
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 7, p. 787 - 792
[3] Patent: US2006/217417, 2006, A1, . Location in patent: Page/Page column 12
[4] Patent: WO2008/89459, 2008, A1, . Location in patent: Page/Page column 61
[5] Patent: WO2015/103355, 2015, A1, . Location in patent: Paragraph 0190
[6] Patent: US2016/115128, 2016, A1, . Location in patent: Paragraph 1377; 1378
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4908 - 4913
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[2] Tetrahedron Letters, 2011, vol. 52, # 4, p. 512 - 514
[3] Patent: WO2014/52365, 2014, A1,
[4] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 8, p. 4442 - 4452
  • 9
  • [ 105-50-0 ]
  • [ 73027-79-9 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 4, p. 512 - 514
[2] Patent: WO2014/52365, 2014, A1,
[3] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 8, p. 4442 - 4452
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  • [ 73027-79-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 7, p. 787 - 792
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Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 7, p. 787 - 792
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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Reference: [1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
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YieldReaction ConditionsOperation in experiment
79%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 2 h;
Stage #2: at 25℃; for 2 h;
A mixture of 4,6-dichloronicotinic acid (20 g, 104 mmol) in DCM (200 mL) was cooled to 0 °C before the addition of DMF (0.807 ml, 10.42 mmol) and oxalyl chloride (10.94 ml, 125 mmol). The resulting reaction was stirred at about 0 °C-25 °C. After about 2h, EtOH (48,7 ml, 833 mmol) was slowly added and stirred at about 25 °C for 2 h. The reaction mixture was diluted with ether (50 mL) and the resulting solution was washed with saturated aqueous NaHC03 (3 x 50 mL). The extracts were combined and dried over anhydrous Na2S04, filtered, and the solvent was removed in vacuo to provide ethyl 4,6-dichloronicotinate (18 g. 79percent): LC/MS (Table 1, Method d) Rt=1.91 min.; MS m/z = 220 (M+H).
Reference: [1] Patent: WO2016/198908, 2016, A1, . Location in patent: Page/Page column 80; 81
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Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1023 - 1040
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 20℃; for 3 h;
Stage #2: With ammonium hydroxide In dichloromethane at 25℃; for 1.5 h;
4,6-Dichloro-nicotinamide (2) (1173) Oxalyl chloride (7.70 mL, 88.3 mmol) was added over 1 hour to a suspension of 4,6-dichloronicotinic acid (8.47 g, 44.1 mmol) in dimethylformamide (200 mL) at room temperature. The reaction mixture was stirred for an additional 3 hours at room temperature then concentrated in vacuo. The residue was dissolved in CH2Cl2 (200 mL) followed by the dropwise addition of NH4OH (8.3 mL, 130 mmol) over 30 minutes [Note: reaction is exothermic upon addition of NH4OH and care was taken to control the rate of addition so that the reaction temperature did not exceed 25° C.]. The reaction mixture was stirred for an additional 1 hour at room temperature then diluted with water (600 mL) and extracted with EtOAc (4×600 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated to give the title compound as a light brown solid (8.05 g, 95percent yield). This material was carried forward without further purification. (1174) 1H NMR 400 MHz (d6-DMSO) δ 8.48 (s, 1H), 8.10 (br s, 1H), 7.87 (br s, 2H).
71%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 3 h;
Stage #2: With ammonia In tetrahydrofuran; water at 0℃; for 1 h;
4,6-Dichloro-nicotinic acid (10.3 g, 53.4 mmol) was suspended in CH2Cl2 (200 mL).
Oxalyl chloride (14 mL, 158 mmol) was added and the reaction was placed in an ice bath. DMF (1.0 mL) was added and the reaction was fitted with an air cooled condenser.
The reaction was stirred for 3 h and allowed to warm to 25° C.
The volatiles were removed in vacuo and the crude residue was resuspended in THF (200 mL) and cooled to 0° C.
To this stirred suspension was added concentrated aqueous ammonia (75 mL) dropwise and the reaction was allowed to stir for 1 h.
The volatiles were removed and the crude was redissolved in EtOAc and poured into brine.
The aqueous phase was separated and extracted twice with EtOAc.
The organic layers were combined, dried (Na2SO4), decanted and concentrated to afford 4,6-dichloro-nicotinamide as a beige solid (7.27 g, 71percent).
Reference: [1] Patent: US2015/291629, 2015, A1, . Location in patent: Paragraph 1173-1174
[2] Patent: US2006/217417, 2006, A1, . Location in patent: Page/Page column 12; 13
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Reference: [1] Patent: US2012/108566, 2012, A1, . Location in patent: Page/Page column 55
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  • [ 70593-57-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4908 - 4913
  • 23
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Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9508 - 9530
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YieldReaction ConditionsOperation in experiment
89% With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere [01366] To a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4,6-dichloropyridine-3-carboxylic acid (95 g, 494.79 mmol, 1.00 equiv) and tetrahydrofuran (1000 mL) followed by the addition of BH3.THF (1 M) (2111 mL, 4.20 equiv) dropwise with stirring at 0°C. The reaction mixture was stirred at 0°C for 30 mm and at room temperature overnight, quenched by the addition of 1000 mL of water/ice, and extracted with 3x1000 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 78.4 g (89percent) of (4,6-dichloropyridin-3-yl)methanol as a white solid.
89% With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere To a 5000-mL 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed 4,6-dichloropyridine-3-carboxylic acid (95 g, 494.79 mmol, 1.00 equiv) and tetrahydrofuran (1000 mL), followed by the addition of BH3.THF (1 M) (2111 mL, 4.20 equiv) dropwise with stirring at 0 °C. The reaction mixture was stirred at 0 °C for 30 min and at room temperature overnight, quenched by the addition of 1000 mL of water/ice, and extracted with 3x1000 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 78.4 g (89percent) of (4,6-dichloropyridin-3-yl)methanol as a white solid.
Reference: [1] Patent: WO2016/128529, 2016, A1, . Location in patent: Paragraph 0980; 0981; 0982
[2] Patent: WO2018/15410, 2018, A1, . Location in patent: Paragraph 0284-0287
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  • [ 716362-10-6 ]
YieldReaction ConditionsOperation in experiment
73% With lithium hydroxide monohydrate In tetrahydrofuran at 20 - 25℃; for 1 h; Step 1[00163j To a solution of 4,6-dichioronicotinic acid (4 g, 20.8 mmol) in methanol (8mL) and tetrahydrofuran (16 mL) was added lithium hydroxide mono-hydrate (2.62 g,62.5 mmol) and the reaction was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure and 12 mL of water was added, the solution was cooled to 0 °C and 1 N hydrochloric acid (aqueous) was added while the solution was agitated resulting in a precipitate. Gradual addition of the acid was continued until the pHmeasured (litmus paper) to be 4. The suspension was then filtered and the solid collected and triturated with diethyl ether for 1 hour. The solid was filtered, dried and collected yielding Intermediate 6 (2.84 g, 73percent). ‘H NMR (400MHz, DMSO-d6) ö 13.23 (br. s., 1H), 8.54 (s, 1H), 7.32 (s, 1H), 3.94 (s, 3H). LC retention time 0.55 mm [J]. MS(Ej m/z: 188 (MHj.
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 7, p. 787 - 792
[2] Patent: WO2014/74660, 2014, A1, . Location in patent: Paragraph 00163
[3] Patent: US2008/319018, 2008, A1, . Location in patent: Page/Page column 25
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Reference: [1] Patent: WO2016/128529, 2016, A1,
[2] Patent: WO2018/15410, 2018, A1,
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  • [ 1187190-69-7 ]
Reference: [1] Patent: US2015/291629, 2015, A1,
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