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Chemical Structure| 209526-98-7
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Product Details of [ 209526-98-7 ]

CAS No. :209526-98-7 MDL No. :MFCD10000856
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :JJNKKECPOPWYNY-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :20537893
Synonyms :

Calculated chemistry of [ 209526-98-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.37
TPSA : 33.12 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) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 0.63
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 4.01 mg/ml ; 0.0279 mol/l
Class : Very soluble
Log S (Ali) : -0.9
Solubility : 18.1 mg/ml ; 0.126 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.514 mg/ml ; 0.00358 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 209526-98-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 209526-98-7 ]

* 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 [ 209526-98-7 ]
  • Downstream synthetic route of [ 209526-98-7 ]

[ 209526-98-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 128072-93-5 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With diisopropyl aluminium hydride In tetrahydrofuran; toluene at 0℃; for 2 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol; toluene at 0 - 20℃; for 3 h;
Stage #3: With methanol; water; sodium sulfate In tetrahydrofuran; diethyl ether; toluene at 20℃;
(1)
Production of (5-chloropyridin-2-yl)methanol:
With cooling with ice, a toluene solution (66 mL, 66.0 mmol) of 1 N diisopropylaluminium hydride was gradually added to a THF solution (40 mL) of ethyl 5-chloropyridine-2-carboxylate (4.05 g, 22.0 mmol) [Heterocycles, 51(11), 2589 (1999)], then stirred at 0°C for 2 hours.
Next, sodium borohydride (832 mg, 22.0 mmol) and methanol (10 mL) were added to the reaction liquid with cooling with ice, and stirred at room temperature for 3 hours.
Ether was added to the reaction liquid, then water (5 mL) and sodium sulfate 10-hydrate were added, and stirred overnight at room temperature.
The insoluble matter was removed from the reaction liquid by filtration through Celite, then the obtained filtrate was concentrated under reduced pressure to obtain the entitled compound (3.14 g, 100 percent).
1H-NMR (400 MHz, CDCl3, δ ppm): 4.75 (2H, s), 7.20-7.30 (1H, m), 7.67 (1H, dd, J=8.0, 2.4 Hz), 8.53 (1H, d, J=2.4 Hz).
74.6%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 20℃;
Ethyl S-chloro^-pyridinecarboxylate (104.0 mg, 0.560 mmol) was dissolved in THF (5.6 mL) and cooled to 00C. The reaction mixture was then slowly treated with lithium aluminum hydride l.OM solution in THF (0.392 μL, 0.392 mmol) and warmed to ambient temperature. The reaction mixture was allowed to stir at ambient temperature for 1 hour and then cooled to 00C. The reaction mixture was then treated with water (15 μL) followed by l.ON NaOH (15 μL) and then water (45 μL). The reaction mixture was warmed to ambient temperature and allowed to stir for 30 minutes. The reaction mixture was diluted with EtOAc, filtered through glass microfibre filter ("GF/F") paper and concentrated. Silica gel chromatography eluting with a gradient of 50percent hexanes/EtOAc to 100percent hexanes/EtOAc provided (5-chloropyridin-2-yl)methanol (60.0 mg, 0.418 mmol, 74.6percent yield).
Reference: [1] Patent: EP1916239, 2008, A1, . Location in patent: Page/Page column 28
[2] Patent: WO2011/25968, 2011, A1, . Location in patent: Page/Page column 41-42
[3] Patent: EP1748048, 2007, A1, . Location in patent: Page/Page column 34
  • 2
  • [ 86873-60-1 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
66.6% With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 16 h; To a solution of 5-chloropicolinic acid (5 g, 31 .7 mmol) in tetrahydrofuran (50 mL) was added borane-dimethylsulfide complex (10 mL) at 0°C and resulting reaction mixture was maintained at rt for 16 h. Cooled the reaction mass to 0°C, excess borane-dimethylsulfide complex was quenched with methanol (15 mL), refluxed for 1 h, concentrated the reaction, diluted in ethyl acetate (150 mL), washed with water (2 x 50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated to afford 3 g (66.6percent yield) of (5-Chloropyridin-2-yl)methanol as a white solid.1H NMR (400 MHz, CDCI3): δ ppm 3.75 (br.s, 1 H), 4.75 (s, 2H), 7.25 (d, J = 8.8 Hz, 1 H), 7.67 (dd, J = 2.2, 6.1 Hz 1 H), 8.53 (d, J = 8.8 Hz, 1 H).
45%
Stage #1: With borane-THF In tetrahydrofuran at 20 - 70℃; for 5 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 2 h;
EXAMPLE 9; (5-Chloropyridin-2-yl)methyl 4-isopropyl-l,4,6,7-tetrahydro-5H-imidazo[4,5-c]- pyridine-5-carboxylate; 5-Chloropyridine-2-carboxylic acid (2.00 g, 12.7 mmol) was dissolved in THF (12 mL) at 0 0C and added to a solution of borane-THF (19.0 mL, 1 M in THF, 19.0 mmol). THF (10 mL) was added and the reaction mixture was warmed to room temperature, stirred for 2 h and heated under reflux at 70 0C for 3 h. The reaction mixture was cooled to 0 0C, quenched with aq 6 M HCl solution (4 mL) and the solution was stirred for 2 h and concentrated in vacuo. The residue was partitioned between H2O (75 mL) and DCM (75 mL). The aq layer was washed with DCM (3 x 75 mL), adjusted to pH 9 with 4 M aqNaOH (3 mL) and extracted with DCM (3 x 75 mL). The organic layers were combined, - -dried (MgSO4) and concentrated in vacuo to give 5-chloropyridine-2-methanol (0.83 g, 45percent) as a brown gum.Analytical HPLC: purity 79.5percent (System B, Rτ = 3.04 min); Analytical LCMS: purity 85percent (System A, Rτ = 1.15 min), ES+: 143.97 [35ClMH]+ and 145.98 [MH 37Cl]+.
Reference: [1] Patent: WO2014/167528, 2014, A1, . Location in patent: Page/Page column 82; 83
[2] Patent: WO2010/31789, 2010, A1, . Location in patent: Page/Page column 31-32
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8013 - 8029
[4] Patent: WO2012/88469, 2012, A1,
  • 3
  • [ 132308-19-1 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; for 2.5 h; To a cooled (00C) solution of methyl δ-chloro^-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml_) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1 N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1 .60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanolTo a cooled (00C) solution of methyl δ-chloro^-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1 NHCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; II. (5-chloro-2-pyridinyl)methanol To a cooled (0°C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 mL) was added NaB (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding IN HC1. The resulting solution was extracted with EtOAc (3 X 300 mL). The combined organic layers were dried (Na2SC>4) and evaporated. Flash chromatography of the residue over silica gel using 10: 1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent yield): FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) δ ppm 8.44 (d, J = 1.60 Hz, 1H), 7.62 (dd, J = 8.40, 2.40 Hz, 1H), 7.25 (d, J = 8.40 Hz, 1H), 4.69 (s, 2 H), 3.83 (s, 1Η).
95% at 20℃; for 4 h; 5-chloro-2(chloromethyl)pyridine; [00372] To a 0 °C solution of 5-chloropicolinic acid (3.00 g, 19.0 mmol) indichloromethane (20 mL) was added sulfurous dichloride (2.78 mL, 38.1 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction was then concentrated to dryness, then reconstituted in dichloromethane (5 mL). Methanol (10 mL) was added to the reaction mixture, and the reaction was allowed to stir at room temperature for 12 hours, after which it was then diluted with water, extracted with ethyl acetate (3 x 50 mL), washed with water, then washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 80g) using 0 to 80percent ethyl acetate in hexanes to afford methyl 5-chloropicolinate was as an off-white solid (2.75 g, 15.2 mmol, 80percent yield ).[00373] To a 0 °C solution of methyl 5-chloropicolinate (2.70 g, 15.7 mmol) in methanol (50 mL) was added sodium borohydride (1.79 g, 47.2 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction mixture was then concentrated to a residue which was treated with 1M hydrochloric acid solution (15 mL), extracted with ethyl acetate (3 x 100 mL), washed with water, then washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 80g) using 0 to 60percent ethyl acetate in hexanes to afford (5-chloropyridin-2-yl)methanol was as an off-white solid (2.15 g, 14.9 mmol, 95percent yield).[00374] To a 0 °C solution of (5-chloropyridin-2-yl)methanol (2.10 g, 14.6 mmol) in dichloromethane (10 mL) was added sulfurous dichloride (1.60 mL, 21.9 mmol) followed by N,N-dimethylformamide (50 μ), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction mixture was then concentrated to a residue which was reconstituted in water (15 mL), ethyl acetate (15 mL), and saturated sodium bicarbonate solution (15 mL). The organic layers were separated and washed with saturated sodium chloride solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 40g) using 0 to 50percent ethyl acetate in hexanes to afford 5-chloro-2(chloromethyl)pyridine as an light brown oil (2.11 g, 13.0 mmol, 89percent yield).
95% With sodium tetrahydroborate In methanol at 20℃; for 1 h; A solution of methyl 5-chloropicolinate (2 g, 1 1 .7 mmol) in MeOH (20 ml) and sodium borohydride (0.89 g, 23.3 mmol) was stirred at rt for 1 h. After reaction was completed, solvent was evaporated. Distilled water was added and the aqueous layer was extracted with dichloromethane (3 x 30 ml). The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 1 .6 g (95percent yield) of (5- Chloropyridin-2-yl) methanol as colourless liquid.1H NMR (400 MHz, CDCI3): δ ppm 3.29 (br s, 1 H), 4.75 (br s, 2H), 7.25 (1 H, merged with CDCI3), 7.67 (d, J = 7.0 Hz, 1 H), 8.52 (s, 1 H).LC-MS: m/z 144.0 (M+H)+.

Reference: [1] Patent: WO2009/76387, 2009, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2010/141538, 2010, A1, . Location in patent: Page/Page column 18-19
[3] Patent: WO2010/141539, 2010, A1, . Location in patent: Page/Page column 18-19
[4] Patent: WO2010/141545, 2010, A1, . Location in patent: Page/Page column 19-20
[5] Patent: WO2010/141540, 2010, A1, . Location in patent: Page/Page column 17-18
[6] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 47; 48
[7] Patent: WO2012/88469, 2012, A1, . Location in patent: Page/Page column 152-153
[8] Patent: WO2014/167528, 2014, A1, . Location in patent: Page/Page column 55; 56
[9] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 3, p. 344 - 348
[10] Patent: US2006/287341, 2006, A1, . Location in patent: Page/Page column 47-48
[11] Patent: US2007/4772, 2007, A1, . Location in patent: Page/Page column 83
  • 4
  • [ 1245426-33-8 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
59% at 20℃; for 2 h; D. (5-Chloropyridin-2-yl)methanol Sodium methoxide (IM in MeOH) (0.162 mL, 0.162 mmol) was added to a solution of (5-chloropyridin-2-yl)methyl benzoate Part C (200 mg, 0.808 mmol) in MeOH (47.5 mL) and stirred at RT for 2.0 h. The solvent was removed in vacuo and the crude product was subjected to flash chromatography (silica gel/DCM-MeOH 100:0 to 90: 10 gradient) to afford (5-chloropyridin-2-yl)methanol 16D (68 mg, 59 percent yield) as an off-white solid. LC-MS, [M + H]+ = 144. 1H NMR (400 MHz, DMSO) δ 8.51 (1 H, d, J= 2.2 Hz), 7.91 (1 H, dd, J= 8.4, 2.6 Hz), 7.49 (1 H, d, J= 8.4 Hz), 5.53 (1 H, t, J= 5.9 Hz), 4.54 (2 H, d, J=6.2 Hz). HPLC-Method 8; 0.76 min.
Reference: [1] Patent: WO2010/104830, 2010, A1, . Location in patent: Page/Page column 107-108
  • 5
  • [ 31181-89-2 ]
  • [ 209526-98-7 ]
Reference: [1] Patent: US2007/105904, 2007, A1, . Location in patent: Page/Page column 115
  • 6
  • [ 31181-73-4 ]
  • [ 209526-98-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
  • 7
  • [ 52313-58-3 ]
  • [ 209526-98-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
  • 8
  • [ 128073-03-0 ]
  • [ 209526-98-7 ]
Reference: [1] Patent: WO2012/88469, 2012, A1,
  • 9
  • [ 89809-64-3 ]
  • [ 209526-98-7 ]
Reference: [1] Patent: US2007/4772, 2007, A1,
  • 10
  • [ 40473-01-6 ]
  • [ 209526-98-7 ]
Reference: [1] Patent: WO2013/166621, 2013, A1,
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