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Chemical Structure| 41667-95-2
Chemical Structure| 41667-95-2
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Product Details of [ 41667-95-2 ]

CAS No. :41667-95-2 MDL No. :MFCD00075181
Formula : C6H3Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RNRLTTNKVLFZJS-UHFFFAOYSA-N
M.W : 192.00 Pubchem ID :247987
Synonyms :

Calculated chemistry of [ 41667-95-2 ]

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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.446 mg/ml ; 0.00232 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.391 mg/ml ; 0.00204 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 : 1.64

Safety of [ 41667-95-2 ]

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 [ 41667-95-2 ]

* 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 [ 41667-95-2 ]
  • Downstream synthetic route of [ 41667-95-2 ]

[ 41667-95-2 ] Synthesis Path-Upstream   1~14

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Reference: [1] Tetrahedron, 2002, vol. 58, # 37, p. 7381 - 7389
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 3001 - 3006
[3] Patent: WO2015/158427, 2015, A1,
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 3837
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YieldReaction ConditionsOperation in experiment
27% With thionyl chloride; ammonia In tetrahydrofuran; <i>N</i>-methyl-acetamide; methanol; dichloromethane a)
5,6-Dichloro-pyridine-3-carbonitrile

To a stirred solution of 5,6-dichloro-pyridine-3-carboxylic acid (1.11 mg, 5.79 mmol) and methylene chloride (1.5 mL) in an ice bath under argon was added oxalyl chloride (4.4 mL, 8.8 mmol) over 25 min followed by 2 drops of dimethylformamide.
The solution was stirred for 5 min, the ice bath was removed, and the solution was stirred for 1.5 h.
The solution was concentrated to yield a white solid.
To the solid was added tetrahydrofuran (5.0 mL) and 7 N ammonia in methanol (4.0 mL, 28.0 mmol).
The solution was stirred for 1 min and then partitioned between deionized water (25 mL) and 1:1 dichloromethane:ethyl acetate (3*50 mL).
The organic layers were concentrated.
To the solid was added thionyl chloride (50 mL) and the solution was refluxed under argon for 69 h.
The solution was concentrated and the residue was purified twice by column chromatography (1:2, hexane:ethyl acetate, then by 1:1, hexane:ethyl acetate) to yield 268 mg (27percent) of the title compound. 1H NMR (CDCl3): 8.59 (d, J=2.20 Hz, 1H), 8.05 (d, J=2.20 Hz, 1H).
Reference: [1] Patent: US2003/45546, 2003, A1,
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Reference: [1] Patent: WO2015/150203, 2015, A1,
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  • [ 54127-30-9 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With borane-THF In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; potassium carbonate In tetrahydrofuranSaturated solution
X-1 (5,6-Dichloropyridin-3-yl)methanol (G=OH, A=5,6-dichloropyrid-3-yl) (R. Graf et al. J. Prakt. Chem. 1932, 134, 177-87); At 0° C., 859 ml (859 mmol) of a 1M solution of borane/tetrahydrofuran complex in tetrahydrofuran are added dropwise to 110 g (573 mmol) of 5,6-dichloronicotinic acid in 250 ml of tetrahydrofuran. The mixture is warmed to room temperature and stirred at this temperature for 3 hours. After cooling to 0° C., the reaction mixture is made alkaline using saturated aqueous potassium carbonate solution, most of the tetrahydrofuran is removed on a rotary evaporator and the residue is extracted repeatedly with ethyl acetate. The combined organic phases are washed with water and saturated aqueous sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressured and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:2) gives 62 g (61percent of theory) of (5,6-dichloropyridin-3-yl)methanol.1H-NMR (CD3CN): δ [ppm]=3.31 (t, 1H), 4.60 (d, 2H), 7.85 (s, 1H), 8.26 (s, 1H)
61% With borane-THF In tetrahydrofuran at 0 - 20℃; At 0° C., 859 ml (859 mmol) of a 1 M solution of borane-tetrahydrofuran complex in tetrahydrofuran are added dropwise to 110 g (573 mmol) of 5,6-dichloronicotinic acid in 250 ml of tetrahydrofuran. The mixture is warmed to room temperature and stirred at this temperature for 3 hours. After cooling to 0° C., the reaction mixture is made alkaline using saturated aqueous potassium carbonate solution, most of the tetrahydrofuran is removed using a rotary evaporator and the residue is extracted repeatedly with ethyl acetate. The combined organic phases are washed with water and saturated aqueous sodium chloride solution and dried over sodium sulphate. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:2) gives 62 g (61percent of theory) of (5,6-dichloropyridin-3-yl)methanol.1H-NMR (CD3CN): δ [ppm]=3.31 (t, 1H), 4.60 (d, 2H), 7.85 (s, 1H), 8.26 (s, 1H)
61% With borane-THF In tetrahydrofuran at 0 - 20℃; At 0° C., 859 ml (859 mmol) of a 1 M solution of boran/tetrahydrofuran complex in tetrahydrofuran are added dropwise to 110 g (573 mmol) of 5,6-dichloro-nicotinic acid in 250 ml of tetrahydrofuran. The mixture is warmed to room temperature and stirred at this temperature for 3 hours. After cooling to 0° C., the reaction mixture is made alkaline using saturated aqueous potassium carbonate solution, most of the tetrahydrofuran is removed using a rotary evaporator and the residue is extracted repeatedly with ethyl acetate. The combined organic phases are washed with water and saturated in aqueous sodium chloride solution and dried over sodium sulphate. The organic phase is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the molar phase mixture ethyl acetate:cyclohexane (1:2), giving 62 g (61percent of theory) of (5,6-dichloropyridin-3-yl)methanol.1H NMR (CD3CN): δ [ppm]=3.31 (t, 1H), 4.60 (d, 2H), 7.85 (s, 1H), 8.26 (s, 1H)
45% With borane-THF In tetrahydrofuran at 0 - 20℃; for 1.83333 h; Method B
2,3-Dichloro-5-(hydroxymethyl)pyridine
borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 52 ml) was added to a stirred solution of 5,6-dichloronicotinic acid (2 g) in tetrahydrofuran (60 ml) over 20 minutes at 0° C.
The reaction mixture was allowed to warm to room temperature over 90 minutes and then cooled to 0° C. and quenched with water (100 ml)..
The solution was saturated with solid sodium chloride and extracted with ethyl acetate and the combined organic extracts were dried and concentrated in vacuo..
The residue was triturated with dichloromethane-50percent ethyl acetate and the solid by-product was removed by filtration..
The filtrate was concentrated in vacuo and purified by column chromatography using isohexane/ethyl acetate (1:1 v/v) as eluent to yield the product as a white solid (820 mg, 45percent). NMR: δ 4.55 (d, 2H), 5.5 (t, 1H), 8.0 (m, 1H), 8.3 (m, 1H); m/z 178.1 (M+H+).

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5620 - 5637
[2] Patent: US2009/181947, 2009, A1, . Location in patent: Page/Page column 39
[3] Patent: US2009/247551, 2009, A1, . Location in patent: Page/Page column 27
[4] Patent: US2010/48646, 2010, A1, . Location in patent: Page/Page column 25
[5] Patent: US6737435, 2004, B1, . Location in patent: Page/Page column 18
[6] Patent: US2008/108667, 2008, A1, . Location in patent: Page/Page column 7
[7] Patent: US2010/240705, 2010, A1,
[8] Patent: US2012/172391, 2012, A1, . Location in patent: Page/Page column 82
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YieldReaction ConditionsOperation in experiment
81% With sodium hydrogencarbonate In tetrahydrofuran; n-heptane; ethyl acetate Part 1
5,6-dichloro-pyridin-3-yl-methanol
A slurry of 5,6-dichloronicotinic acid (25.3 g, 132 mmol) in THF (30 mL, 4.4 M) is cooled to 0° C. and carefully treated with 2 M borane dimethyl sulfide/THF (100 mL, 200 mmol) via syringe under a stream of nitrogen.
After 1 h, the cooling bath is removed.
After stirring overnight the colution is re-cooled to 0° C. and carefully quenched with water (20 mL).
The reaction volume is reduced in vacuo, 50percent NaHCO3 (150 mL) is added and the mixture is extracted with ethyl acetate (2*150 mL).
The organic layer is washed with saturated aq NaCl (100 mL) and dried over Na2SO4.
The product is purified by MPLC (30-90percent ethyl acetate in n-heptane) to provide 5,6-dichloro-pyridin-3-yl-methanol as a white solid (19.1 g, 81percent): Rf 0.57 (25percent ethyl acetate in n-heptane), 1H NMR (CDCl3, 300 MHz) δ8.27 (d, J=2.3 Hz, 1 H), 7.84 (d, J=2.3 Hz, 1 H), 4.74 (s, 2 H); ESI-LCMS m/z calcd for C6H5Cl2NO: 177.0; found 178.0 (M+1)+.
Reference: [1] Patent: US2003/166668, 2003, A1,
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YieldReaction ConditionsOperation in experiment
97% for 18 h; Heating / reflux Example 7: Preparation of 5,6-dichloro-nicotinic acid methyl ester (10)[284] 4.45 niL of sulfuric acid was added to 5.0 g of 5,6-dichloronicotinic acid (26 mmol) dissolved in 50 niL of methanol, and refluxed under heating and stirring for 18 hours. The mixture was cooled to 40C, neutralized with a saturated sodium bicarbonate solution, and methanol was concentrated under reduced pressure. The aqueous layer was extracted with ethyl acetate, and the organic layer was separated to be dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=20/l) to obtain 5.2 g of white solid, 5,6-dichloro-nicotinic acid methyl ester (yield 97percent).[285] 1H NMR (CDCl3) δ: 8.86 (s, IH), 8.34 (s, IH), 3.96 (s, 3H)
97%
Stage #1: for 18 h; Reflux
Stage #2: at 4℃;
Example 7Preparation of 5,6-dichloro-nicotinic acid methyl ester (10)4.45 mL of sulfuric acid was added to 5.0 g of 5,6-dichloronicotinic acid (26 mmol) dissolved in 50 mL of methanol, and refluxed under heating and stirring for 18 hours. The mixture was cooled to 4° C., neutralized with a saturated sodium bicarbonate solution, and methanol was concentrated under reduced pressure. The aqueous layer was extracted with ethyl acetate, and the organic layer was separated to be dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=20/1) to obtain 5.2 g of white solid, 5,6-dichloro-nicotinic acid methyl ester (yield 97percent).1H NMR (CDCl3) δ: 8.86 (s, 1H), 8.34 (s, 1H), 3.96 (s, 3H)
96%
Stage #1: With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 5 h;
Stage #2: for 1 h; Heating / reflux
5,6-Dichloro-nicotinic acid methyl esterA solution of 5,6-dichloro-nicotinic acid (55.0 g, 281 mmol) in SOCI2 (204 ml) was treated with DMF (0.1 ml) and the mixture was heated to 80 0C for 5 h. The excess of SOCI2 was evaporated and the crude product was taken up in MeOH (300 ml) and the resulting solution was heated to reflux for 1 h. The mixture was then allowed to cool slowly to RT. 5,6-Dichloro- nicotinic acid methyl ester precipitated and was collected by filtration (55.6 g, 96percent). UPLC (5-100percent CH3CN): tR = 1.384 min, TLC (Hex/EtOAc 1 :1 ): Rf = 0.76.
34.7% at 0℃; for 3 h; Reflux Thionyl chloride (27.9 g, 234 mmol) was added dropwise to the solution of 5,6-dichloropyridine-3-carboxylic acid (18.0 g, 94 mmol) in MeOH (300 mL) at 0 °C. The resulting mixture was heated under reflux for 3 hours, cooled and concentrated under reduced pressure. The residue was purified by silica chromatography (hexane:EtOAc = 5:1 to 3:1) to give the title compound (6.7 g, 34.7percent yield) as a white solid. MS mlz 226.08 [M+Hjt
5 g at 25℃; A mixture of 5 6-dichloronicotinic acid (5 g) and sulfurous dichloride (3.10 g) in methanol (20 mL) was stirred at 25overnight. Cold water (100 mL) was added and the resulting mixture was neutralized with sat. NaHCO3solution. The aqueous layer was extracted with DCM (2×100 mL) and the combined organic layers were dried over Na2SO4. Aftet filtration the filtrate was concentrated in vacuo to give the title compound (5 g) as a white solid. MS (ESI) C7H5Cl2NO2requires 205 found 206 [M+H]+.
5 g at 25℃; A mixture of 5,6-dichloronicotinic acid (5 g) and sulfurous dichloride (3.10 g) in methanol (20 mL) was stirred overnight at 25°C. Cold water (100 mL) was added and the resulting mixture was neutralized with sat. NaHCO3 solution. The aqueous layer was extracted with DCM (2x 100 mL) and the combined organic layers were dried over Na2SO4. Aftet filtration, the filtrate was concentrated in vacuo to give the title compound (5 g) as white solid. MS (ESI): C7H5C12NO2requires 205; found 206 [M+H].
5 g at 25℃; Description 123Methyl 5,6-dichioronicotinate (P123) The mixture of 5,6-dichloronicotinic acid (5 g) and sulfurous dichloride (3.10 g) in methanol (20 mL) was stirred overnight at 25°C. Cold water (100 mL) was added and the resulted mixture wasneutralized with saturated NaHCO3 solution. The aqueous layer was extracted with DCM (2x 100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum to afford the title compound (5 g) as white solid. MS (ESI): C7H5C12NO2 requires 205; found 206 [M+H].
5 g at 25℃; Take 5,6-dichloronicotinic acid (5 g) with thionyl chloride(sulfbrous dichloride) (3.10 g)In methanol (20 mL) was stirred at 25 ° C overnight. Add cold water (100 mL) and the resulting mixture was neutralized with saturated NaHCO3 solution. The aqueous layer was extracted with DCM (2 x 100 mL) and the combined organic layers were dehydrated by Na2S04. After filtration, the filtrate was concentrated in vacuo to give the title compound (5 g) as a white solid.

Reference: [1] Patent: WO2008/7900, 2008, A1, . Location in patent: Page/Page column 15; 26
[2] Patent: US2009/209540, 2009, A1, . Location in patent: Page/Page column 15; 7
[3] Patent: WO2008/128968, 2008, A1, . Location in patent: Page/Page column 51
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3719 - 3742
[5] Patent: WO2018/165385, 2018, A1, . Location in patent: Paragraph 00391
[6] Patent: WO2004/35549, 2004, A1, . Location in patent: Page 182
[7] Patent: WO2014/28669, 2014, A1, . Location in patent: Paragraph 00313
[8] Patent: WO2015/180614, 2015, A1, . Location in patent: Page/Page column 22
[9] Patent: WO2015/180613, 2015, A1, . Location in patent: Page/Page column 14
[10] Patent: WO2015/180612, 2015, A1, . Location in patent: Page/Page column 76; 77
[11] Patent: TW2017/14884, 2017, A, . Location in patent: Paragraph 0063
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YieldReaction ConditionsOperation in experiment
100% at 0℃; for 12 - 18 h; To a 25OmL reaction vessel was added 5,6-dichloronicotinic acid (15.6mmol), toluene (5OmL), and methanol (50 mL). The reaction mixture was cooled to 00C and a 2M solution of trimethylsilyldiazomethane in hexanes (23.4mmol) was subsequently added dropwise followed by stirring for about 12-18 hours. Concentration of the reaction mixture to dryness afforded the desired product (3.2g) as an off-white solid; MW = 206.03, yield = 100percent, HPLC (min) = 3.96, LC-MS = 206, 208; dichloro fragment
100% at 0℃; for 12 - 18 h; Preparation B: Reaction 1 : Methyl 5, δ-dichloropyridine-S-carboxylateTo a 25OmL reaction vessel was added 5,6-dichloronicotinic acid (15.6mmol), toluene (5OmL), and methanol (50 mL). The reaction mixture was cooled to 0°C and a 2M solution of trimethylsilyldiazomethane in hexanes (23.4mmol) was subsequently added dropwise followed by stirring for about 1-2-18 hours. Concentration of the reaction mixture to EPO <DP n="46"/>dryness afforded the desired product (3.2g) as an off-white solid; MW = 206.03, yield = 100percent, HPLC (min) = 3.96, LC-MS = 206, 208; dichloro fragment.
Reference: [1] Patent: WO2007/4038, 2007, A1, . Location in patent: Page/Page column 51
[2] Patent: WO2007/36769, 2007, A1, . Location in patent: Page/Page column 44-45
[3] Patent: WO2005/58848, 2005, A1, . Location in patent: Page/Page column 53-54
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Reference: [1] Patent: US2002/19527, 2002, A1,
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YieldReaction ConditionsOperation in experiment
91%
Stage #1: With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 0.5 h;
Stage #2: With hydrogenchloride In water
A mixture of ethyl 5,6-dichloronicotinate (1.0 g, 4.5 mmol) and aqueous NaOH (2 N, 6.75 mL, 13.5 mmol) in a mixed solvents of THF/MeOH/water (50 mL, 4/1/1) was stirred at room temperature for 0.5 h.
After concentration, the mixture was acidified with 2 N HCl to pH around 2.
The resulting mixture was extracted with ether (30 mL*3).
The organic layer was washed with water (50 mL*3), dried over Na2SO4, and concentrated to afford 5,6-dichloronicotinic acid (800 mg, 91percent yield) as a white solid. LCMS (ESI) m/z: 192.0 [M+H]+.
Reference: [1] Patent: US2013/317000, 2013, A1, . Location in patent: Paragraph 0368-0369
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Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 127,129
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Reference: [1] Chemische Berichte, 1904, vol. 37, p. 3830
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Reference: [1] Patent: WO2013/123444, 2013, A1,
[2] Patent: WO2008/132600, 2008, A2,
[3] Patent: WO2008/133973, 2008, A1,
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Reference: [1] Patent: US2011/212998, 2011, A1,
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