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Product Details of [ 71690-05-6 ]

CAS No. :71690-05-6 MDL No. :MFCD08448226
Formula : C6H3Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :ROSCFXKNBQZLFC-UHFFFAOYSA-N
M.W : 176.00 Pubchem ID :11535654
Synonyms :

Calculated chemistry of [ 71690-05-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.64
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 1.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.518 mg/ml ; 0.00294 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.13 mg/ml ; 0.0064 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.2
Solubility : 0.111 mg/ml ; 0.000628 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 71690-05-6 ]

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 [ 71690-05-6 ]

* 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 [ 71690-05-6 ]
  • Downstream synthetic route of [ 71690-05-6 ]

[ 71690-05-6 ] Synthesis Path-Upstream   1~5

  • 1
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  • [ 71690-05-6 ]
YieldReaction ConditionsOperation in experiment
90% With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxymethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CH2Cl2 (150 mL). The reaction mixture was stirred at a temperature of about 25° C. for 48 h, filtered through CELITE, and concentrated under reduced pressure. The mixture was chromatographed by a silica gel chromatography column eluting with a gradient of ethyl acetate (0percent-40percent)/hexanes to provide 7.2 g of 4 (90percent yield). 1H NMR (400 MHz, CDCl3) δ 10.08 (1H, s), 8.77 (1H, d, J=1.97 Hz), 8.25 (1H, d, J=1.97 Hz). LC/MS (M+1): 176.
90% With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxylmethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CH2Cl2 (150 mL). The reaction mixture was stirred at a temperature of about 25° C. for 48 h, filtered through CELITE, and concentrated under reduced pressure. The mixture was chromatographed by a silica gel chromatography column eluting with a gradient of ethyl acetate (0percent-40percent)/hexanes to provide 7.2 g of 4 (90percent yield). 1H NMR (400 MHz, CDCl3) δ 10.08 (1H, s), 8.77 (1H, d, J=1.97 Hz), 8.25 (1H, d, J=1.97 Hz). LC/MS (M+1): 176.
90% With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxylmethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CH2Cl2 (150 mL). The reaction mixture was stirred at a temperature of about 25° C. for 48 h, filtered through CELITE, and concentrated under reduced pressure. The mixture was chromatographed by a silica gel chromatography column eluting with a gradient of ethyl acetate (0percent-40percent)/hexanes to provide 7.2 g of 4 (90percent yield). 1H NMR (400 MHz, CDCl3) δ 10.08 (1H, s), 8.77 (1H, d, J=1.97 Hz), 8.25 (1H, d, J=1.97 Hz). LC/MS (M+1): 176.
90% With manganese(IV) oxide In dichloromethane at 25℃; for 48 h; 2,3-Dichloro-5-formylpyridine. To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxylmethylpyridine (64, 8.10 g, 50.0 mmol) in anhydrous CH2CIo ( 150 mL). The reaction mixture was stirred at a temperature of about 250C for 48 h, filtered through CELITE, and concentrated under reduced pressure. The mixture was chromatographed by a silica gel chromatography column eluting with a gradient of ethyl acetate (0percent-40percent)/hexanes to provide 7.2 g of 65 (90percent yield). 1H NMR (400 MHz, CDCl3) δ 10.08 (IH, s), 8.77 (I H, d, J=1.97 Hz), 8.25 (IH, d, J=1.97 Hz). LC/MS (M+1 ): 176.
90% With manganese(IV) oxide In dichloromethane at 20℃; for 48 h; To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxylmethylpyridine (1, 8.10 g, 50.0 mMol) in <n="70"/>anhydrous CH2Cl2 (150 mL). The resulting mixture was stirred at room temperature for 2 days, which was filtered through Celite and concentrated. The crude mixture was purified by a silica gel chromatography column eluting with a gradient of ethyl acetate (0-40percent)/hexanes to give 7.2 g of the desired product 2 (90percent). 1H NMR (400 MHz, CDCl3) δ 10.08 (1 H, s), 8.77 (1 H, d, J = 1.97 Hz), 8.25 (1 H, d, J = 1.97 Hz). LC/MS (M+l): 176.
88% With Dess-Martin periodane In dichloromethane at 0℃; for 0.5 h; Inert atmosphere To a solution of (5,6-dichloropyridin-3-yl)methanol (23) (1 g, 5.62 mmol) in CH2Cl2 (40 ml) was added Dess-Martin (2.6 g, 6.18 mmol) at 0° C. under nitrogen. (0747) After being stirred for 30 min at 0° C., the reaction mixture was quenched with sat. NaHCO3 and diluted with CH2Cl2. The resulting organic layer was separated and the aqueous layer was extracted with CH2Cl2, the combined organic layers were washed with Na2S2O3, H2O and brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with CHCl3. The resulting solid was filtered through a glass funnel, rinsed with CHCl3. The liquid residue was chromatographed on silica gel eluting with a gradient of hexane/ethyl acetate (10-20percent) to afford 867 mg of the desired product (24) in 88percent yield as a white solid. 1H-NMR (DMSO-d6) δ: 10.09 (1H, s), 8.90 (1H, s), 8.55 (1H, s). LC/MS (M+1): 176.
22%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.166667 h; Molecular sieve
Stage #2: With tetrapropylammonium perruthennate In dichloromethane
To a solution of (5,6-dichloro-3-pyridinyl)methanol (200 mg) in CH2Cl2, molecular sieves (3A) (55 mg) and 4-methy-morpholine-N-oxide (198 mg) was added and stirred at room temperature for 10 minutes. Then tetra-n-propylammonium perruthenate(VII) (38 mg) was added and stirred overnight. The reaction mixture was filtered and the solvent was evaporated to dryness under vacuum. The residue obtained was purified by chromatography column on silica gel using a mixture of EtOAc/hexane as eluent to give 44 mg (22percent) of the title compound. 1H-NMR (δ, ppm, CDCl3): 10.09 (s, 1 H), 8.77 (s, 1 H), 8.25 (s, 1 H).
22%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.166667 h; Molecular sieve
Stage #2: With tetrapropylammonium perruthennate In dichloromethane
Preparation 2; 5,6-Dichloro-3-pyridinecarbaldehyde (Used to prepare Example 15) To a solution of (5,6-dichloro-3-pyridinyl)methanol (200 mg) in DCM, molecular sieves (3A) (55 mg) and 4-methyl-morpholine-N-oxide (198 mg) was added and stirred at room temperature for 10 minutes. Then tetra-n-propylammonium perruthenate (VII) (38 mg) was added and stirred overnight. The reaction mixture was filtered and the solvent was evaporated to dryness under vacuum. The residue obtained was purified by chromatography column on silica gel using a mixture of EtOAc/hexane as eluent to give 44 mg (22percent) of the title compound.1H-NMR (δ, ppm, CDCl3): 10.09 (s, 1H), 8.77 (s, 1H), 8.25 (s, 1H).

Reference: [1] Patent: US2010/120862, 2010, A1, . Location in patent: Page/Page column 94
[2] Patent: US2010/137306, 2010, A1, . Location in patent: Page/Page column 169
[3] Patent: US2010/130499, 2010, A1, . Location in patent: Page/Page column 122
[4] Patent: WO2008/132600, 2008, A2, . Location in patent: Page/Page column 258
[5] Patent: WO2008/133973, 2008, A1, . Location in patent: Page/Page column 68-69
[6] Patent: US9156830, 2015, B2, . Location in patent: Page/Page column 91-92
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3719 - 3742
[8] Patent: EP2080761, 2009, A1, . Location in patent: Page/Page column 39-40
[9] Patent: US2009/306089, 2009, A1, . Location in patent: Page/Page column 25-26
[10] Patent: WO2004/35549, 2004, A1, . Location in patent: Page 164
[11] Patent: WO2010/92342, 2010, A1, . Location in patent: Page/Page column 48
[12] Patent: WO2011/79305, 2011, A1, . Location in patent: Page/Page column 43
[13] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3793 - 3816
  • 2
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YieldReaction ConditionsOperation in experiment
75% With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 0.5 h; A 2M solution of LiAIH4 in THF (1 9.2mL, 38.2gmmol) was added to a solution of 5,6-dichloro-N-methoxy-N-methylnicotinamide (22g, 76.59mo1) in THE (360mL) at -78°C and stirred for 30 mm at sametemperature. The RM was quenched with sat. Na2SO4 solution and filtered the salts through celite bed, washed with EtOAc. The filtrate was dried (anhydr. Na2SO4), filtered and evaporated the solvent under vacuo to give crude as a thick liquid. The crude was purified by CC (0-5percent EtOAc in PE) to give 12g (75percent) of 5,6-dichloronicotinaldehyde as liquid.
Reference: [1] Patent: WO2015/158427, 2015, A1, . Location in patent: Page/Page column 90; 91
[2] Patent: WO2008/75757, 2008, A1, . Location in patent: Page/Page column 36
  • 3
  • [ 41667-95-2 ]
  • [ 71690-05-6 ]
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,
  • 4
  • [ 54127-29-6 ]
  • [ 71690-05-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. &lt;2&gt;134, p. 177,184
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 3001 - 3006
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. &lt;2&gt;134, p. 177,184
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