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[ CAS No. 101990-70-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 101990-70-9
Chemical Structure| 101990-70-9
Chemical Structure| 101990-70-9
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Product Details of [ 101990-70-9 ]

CAS No. :101990-70-9 MDL No. :MFCD10697570
Formula : C7H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :YNCJGPOTUFPVTB-UHFFFAOYSA-N
M.W : 157.60 Pubchem ID :13752891
Synonyms :

Calculated chemistry of [ 101990-70-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.49
TPSA : 22.12 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.23
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.24 mg/ml ; 0.00784 mol/l
Class : Soluble
Log S (Ali) : -1.62
Solubility : 3.74 mg/ml ; 0.0238 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.109 mg/ml ; 0.000692 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 101990-70-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 UN#:3261
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 101990-70-9 ]

* 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 [ 101990-70-9 ]
  • Downstream synthetic route of [ 101990-70-9 ]

[ 101990-70-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 58584-63-7 ]
  • [ 101990-70-9 ]
YieldReaction ConditionsOperation in experiment
100% With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1 h; Inert atmosphere j0259j To a stirred solution of (6-methoxypyridin-3-yl)methanol (75 mg, 0.54 mmol) in dichloromethane (2 mL) under nitrogen was added triethylamine (0.083 mL, 0.59 mmol) followed by methanesulfonyl chloride (0.044 mL, 0.57 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was partitioned between dichioromethane (10 mL) and water (10 mL). The organic extract was dried over sodium sulfate, filtered and concentrated to give the title compound 88 mg (quantitative yield) as a yellow oil.Tr(METCR1278) = 1.63 mm, (ESj (M-J-H) 1581160.
96% With thionyl chloride In toluene at 20℃; for 1 h; Inert atmosphere Under nitrogen, thionyl chloride (2.05mL, 3.34g, 28.09mmol) was added to a solution of (6-methoxy-pyridin-3-yl)methanol 2c (3.56g, 25.60mmol) in dry toluene (10.6mL) and the solution was stirred at room temperature for 1h before NaOH (2M, 10mL) was added. The solution was stirred for 10min before extraction with toluene (2×20mL). The organic extracts were washed water and concentrated under reduced pressure to give the product 24 (3.85g, 24.52mmol, 96percent yield) as a yellow oil; δH (400MHz, CDCl3) 8.15 (1H, d, J 2.7, H3), 7.62 (1H, dd, J 8.5, 2.7, H2), 6.75 (1H, d, J 8.5, H1), 4.55 (2H, s, H4), 3.94 (3H, s, CH3); δC (101MHz, CDCl3) 163.6, 146.7, 139.2, 126.1, 111.3, 53.6, 43.3.
91.4% With thionyl chloride In N,N-dimethyl-formamide at 0℃; for 2.3 h; Preparation Example 2
Synthesis of 5-chloromethyl-2-methoxypyridine (3)
To a solution of (6-methoxypyridin-3-yl)methanol (2) (537.8 g, 3.86 mol) obtained in Preparation Example 1 in dimethylformamide (1.6 L) was added dropwise thionyl chloride (310 mL, 4.25 mol) over a period of 1.3 hours while cooling in an ice bath under a nitrogen atmosphere.
After stirring for 1 hour while cooling in an ice bath, toluene (5.4 L) and a 2N aqueous solution of sodium hydroxide (5.4 L) were added successively to the reaction mixture at 23° C. or below.
The reaction mixture was stirred for about 10 minutes and then the aqueous layer was separated, the organic layer was washed with water (2.7 L).
The organic layer was concentrated under reduced pressure to dryness, and then toluene (1.0 L) was added to the residue and azeotropic distillation was carried out to give 618.8 g of the title compound as a pale yellow oil (content 556.3 g, yield 91.4percent).
1H-NMR (CDCl3) δ (ppm): 8.15 (1H, d, J=2.4 Hz), 7.63 (1H, dd, J=2.4 Hz, 8.4 Hz), 6.75 (1H, d, J=8.4 Hz), 4.55 (2H, s), 3.94 (3H, s)
88%
Stage #1: With thionyl chloride In dichloromethane at 20℃;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane
Step 2:
5-Chloromethyl-2-methoxy-pyridine
Thionyl chloride (9.2 mL, 126 mmol) was added dropwise to a solution of (6-methoxy-pyridin-3-yl)-methanol (1.00 g, 7.2 mmol) in dichloromethane (38 mL).
The reaction mixture was stirred at room temperature overnight.
The solvent was evaporated and dichloromethane (100 mL) was added.
The solution was washed with saturated aqueous sodium hydrogen carbonate (this resulted in bubbling).
The organic layer was separated and the aqueous layer was extracted with dichloromethane (2*100 mL).
The combined organic layers were washed with brine (150 mL), dried (sodium sulfate), filtered, and evaporated to give 5-chloromethyl-2-methoxy-pyridine (995 mg, 88percent) as a clear oil.
88%
Stage #1: With thionyl chloride In dichloromethane at 0 - 20℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Step B: Preparation of 5-(Chloromethyl)-2-methoxypyridine. Thionyl chloride (0.23 ml, 3.23 mmol) was added to a solution of (6-methoxypyridin-3-yl)methanol (1.10 g, 8.41 mmol) in DCM at 0° C. and the reaction mixture was stirred for 2 h at room temperature. After completion of reaction, the volatiles were evaporated and the reaction mixture was basified with saturated sodium bicarbonate solution. The compound was extracted with DCM (2.x.30 ml) and washed with brine (15 ml). The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and dried to afford 1.1 g (88percent) of 5-(chloromethyl)-2-methoxypyridine as a colorless liquid. This compound was directly taken to the next step.
0.58 g With thionyl chloride In dichloromethane at 0 - 30℃; for 2 h; Inert atmosphere To a solution of 2-methoxy-5-hydroxymethylpyridine (0.71 g, 0.005mole) in DCM (5 mL) at 0 °C under N2, was added thionyl chloride (0.7 mL, 0.009 mole) drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was diluted with DCM (50 mL) and treated with saturated aqueous sodium bicarbonate (10 mL). Organic layer was washed with water (20 mL), brine solution (20 mL), dried over Na2SC>4 and concentrated under vacuum to obtain the title compound. Yield: 0.58 g; lH - NMR (CDC13, 400 MHz) δ ppm: 3.94 (s, 3H), 4.55 (s, 2H), 6.75 - 6.77 (d, J = 8.5 Hz, 1H), 7.61 - 7.64 (dd, J = 2.2, 8.5 Hz, 1H), 8.14 (s, 1H); Mass (m/z): 158.0 - 160.0 (M+H) +.

Reference: [1] Patent: WO2016/33445, 2016, A1, . Location in patent: Paragraph 0259
[2] Tetrahedron, 2014, vol. 70, # 40, p. 7207 - 7220
[3] Patent: US2006/235225, 2006, A1, . Location in patent: Page/Page column 4
[4] Patent: US2007/49632, 2007, A1, . Location in patent: Page/Page column 38
[5] Patent: US2011/224225, 2011, A1, . Location in patent: Page/Page column 23
[6] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4636 - 4645
[7] Patent: US2010/179321, 2010, A1, . Location in patent: Page/Page column 4
[8] Organic Letters, 2010, vol. 12, # 21, p. 5004 - 5007
[9] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
[10] Journal of Organic Chemistry, 2011, vol. 76, # 20, p. 8336 - 8346
[11] Patent: WO2011/159554, 2011, A1, . Location in patent: Page/Page column 31
[12] Patent: WO2011/159553, 2011, A1, . Location in patent: Page/Page column 28
[13] Patent: WO2011/84368, 2011, A1, . Location in patent: Page/Page column 55
[14] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
[15] Patent: WO2018/42362, 2018, A1, . Location in patent: Page/Page column 41
  • 2
  • [ 65873-72-5 ]
  • [ 101990-70-9 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 1 h;
Stage #2: With ammonium chloride In methanol; water
Reference Example 28Step 15-chloromethyl-2-methoxypyridine (Compound A80)2-methoxy-5-pyridinecarbaldehyde (137 mg, 0.999 mmol) was dissolved in methanol (5.0mL). To this, sodium borohydride (37.8 mg, 0.999 mmol) was added at 0°C, and the mixture was stirred for 1 hour. To the reaction mixture, a saturated ammonium chloride aqueous solution was added, and extraction with ethyl acetate was performed twice. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was dissolved in dichloromethane (5.0 mL). To this, triethylamine (278 μL, 2.00 mmol) and methanesulfonyl chloride (116 μL, 1.50 mmol) were added, and the mixture was stirred overnight. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, extraction with chloroform was performed twice. The organic layer was dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography to give Compound A80 (116 mg, yield: 74percent). ESI-MS: m/z 158 [M + H]+; 1H NMR (CDCl3)δ(ppm): 3.94 (s, 3H), 4.55 (s, 2H), 6.76 (d, J = 8.4 Hz, 1H), 7.62 (dd, J = 2.4, 8.4 Hz, 1H), 8.15 (d, J = 2.4 Hz, 1H).
Reference: [1] Patent: EP2308880, 2011, A1, . Location in patent: Page/Page column 56
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4721 - 4734
  • 3
  • [ 26218-80-4 ]
  • [ 101990-70-9 ]
Reference: [1] Patent: US2011/224225, 2011, A1,
[2] Journal of Organic Chemistry, 2011, vol. 76, # 20, p. 8336 - 8346
[3] Patent: WO2011/159554, 2011, A1,
[4] Patent: WO2011/159553, 2011, A1,
[5] Patent: WO2011/84368, 2011, A1,
[6] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
[7] Tetrahedron, 2014, vol. 70, # 40, p. 7207 - 7220
  • 4
  • [ 66572-55-2 ]
  • [ 101990-70-9 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4636 - 4645
[2] Tetrahedron, 2014, vol. 70, # 40, p. 7207 - 7220
  • 5
  • [ 5006-66-6 ]
  • [ 101990-70-9 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4636 - 4645
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