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[ CAS No. 63071-12-5 ]

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Chemical Structure| 63071-12-5
Chemical Structure| 63071-12-5
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Product Details of [ 63071-12-5 ]

CAS No. :63071-12-5 MDL No. :MFCD08235128
Formula : C7H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OPXGBIUWGAUTER-UHFFFAOYSA-N
M.W :139.15 Pubchem ID :12325389
Synonyms :

Calculated chemistry of [ 63071-12-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.86
TPSA : 42.35 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) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 0.31
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.21
Solubility : 8.58 mg/ml ; 0.0617 mol/l
Class : Very soluble
Log S (Ali) : -0.76
Solubility : 24.1 mg/ml ; 0.173 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.95
Solubility : 1.55 mg/ml ; 0.0111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 63071-12-5 ]

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

Application In Synthesis of [ 63071-12-5 ]

* 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 [ 63071-12-5 ]
  • Downstream synthetic route of [ 63071-12-5 ]

[ 63071-12-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 26256-72-4 ]
  • [ 63071-12-5 ]
YieldReaction ConditionsOperation in experiment
30% With sodium tetrahydroborate In methanol; water at 0 - 20℃; for 1.5 h; Inert atmosphere Methyl-6-methoxypyridine-2-carboxylate (2 g, 11.96 mmol) in anhydrous methanol (20 mL) was cooled to 0° C. under nitrogen and sodium borohydride (1.36 g, 35.89 mmol) was slowly added to the solution. The reaction was left stirring at 0° C. for 30 minutes, then allowed to warm up to room temperature for 1 hour. The reaction was quenched with water and concentrated on the rotovap. The reaction was diluted with brine (100 mL) and extracted with dichloromethane/2-propanol solution (2:1) (3*, 150 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated on the rotovap to afford (6-methoxypyridin-2-yl)methanol (500 mg, 30percent) as an oil. MS M+H calculated 140.1. Found 140.1.
30% at 0 - 20℃; for 1.5 h; Inert atmosphere Example 75a
(6-Methoxypyridin-2-yl)methanol
Methyl-6-methoxypyridine-2-carboxylate (2 g, 11.96 mmol) in anhydrous methanol (20 mL) was cooled to 0° C. under nitrogen and sodium borohydride (1.36 g, 35.89 mmol) was slowly added to the solution.
The reaction was left stirring at 0° C. for 30 minutes, then allowed to warm up to room temperature for 1 hour.
The reaction was quenched with water and concentrated on the rotovap.
The reaction was diluted with brine (100 mL) and extracted with dichloromethane/2-propanol solution (2:1) (3*, 150 mL).
The combined organic extracts were dried over magnesium sulfate, filtered and concentrated on the rotovap to afford (6-methoxypyridin-2-yl)methanol (500 mg, 30percent) as an oil. MS M+H calculated 140.1. found 140.1.
10% With lithium aluminium tetrahydride In diethyl ether at 20℃; for 4 h; To a solution of the compound (730 mg, 4.37 mmol) prepared in step 1) in diethylether was dropwise added lithium aluminum hydride (175 mg, 4.37 mmol), followed by stirring at room temperature for 4 hrs. Celite (1.5 g) and sodium sulfate decahydrate (0.8 g) were dropwise added to the reaction mixture, and stirred for 10 min at room temperature. The reaction mixture was filtered, and extracted with diethylether. The organic layers were pooled and 'subjected to vacuum filtration and vacuum distillation. The residue was purified using column chromatography (ethyl acetate :hexane = 1 :3) to obtain the desired compound (55 mg, 10percent).
Reference: [1] Patent: US2009/274632, 2009, A1,
[2] Patent: US9247759, 2016, B2, . Location in patent: Page/Page column 303
[3] Patent: US2016/376263, 2016, A1, . Location in patent: Paragraph 0469; 0470
[4] Patent: WO2014/3483, 2014, A1, . Location in patent: Page/Page column 34
[5] Patent: WO2011/79076, 2011, A1, . Location in patent: Page/Page column 93
[6] Patent: WO2012/40230, 2012, A1, . Location in patent: Page/Page column 87
[7] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0527; 0528
  • 2
  • [ 26893-73-2 ]
  • [ 63071-12-5 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: With water; rochelle salt In tetrahydrofuran at 20℃; for 1 h;
Step A: Preparation of (6-methoxypyridin-2-yl)methanol: A cold solution of6-methoxypicolinic acid (1.8 g, 11.8 mmol) in tetrahydrofuran (0.3M, 40 mL) was treated with lithium aluminum hydride (11.8 mL, 11.8 mmol) at 0 °C. This mixture was stirred at 0 °C for 30 minutes, poured into a beaker containing aqueous saturated Rochelle's salt and stirring at ambient temperature continued for 1 hour. The product was extracted from EtO Ac, dried (phase separator silicone treated filter paper) paper, concentrated (1.13 g, 69percent yield) as a clear oil.
Reference: [1] Patent: WO2012/82689, 2012, A1, . Location in patent: Page/Page column 133
[2] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 577
  • 3
  • [ 40473-07-2 ]
  • [ 68-12-2 ]
  • [ 63071-12-5 ]
Reference: [1] Patent: WO2011/28395, 2011, A1, . Location in patent: Page/Page column 20-21
  • 4
  • [ 107465-28-1 ]
  • [ 63071-12-5 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 30, p. 3543 - 3546
[2] Tetrahedron, 1988, vol. 44, # 10, p. 3005 - 3014
  • 5
  • [ 107465-26-9 ]
  • [ 63071-12-5 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 10, p. 3005 - 3014
[2] Tetrahedron Letters, 1986, vol. 27, # 30, p. 3543 - 3546
  • 6
  • [ 77134-17-9 ]
  • [ 63071-12-5 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 30, p. 3543 - 3546
  • 7
  • [ 19621-92-2 ]
  • [ 63071-12-5 ]
Reference: [1] Patent: WO2014/3483, 2014, A1,
[2] Patent: WO2011/79076, 2011, A1,
  • 8
  • [ 40473-07-2 ]
  • [ 63071-12-5 ]
Reference: [1] Patent: WO2012/40230, 2012, A1,
[2] Patent: WO2013/142269, 2013, A1,
  • 9
  • [ 83621-01-6 ]
  • [ 63071-12-5 ]
Reference: [1] Patent: WO2012/40230, 2012, A1,
[2] Patent: WO2013/142269, 2013, A1,
  • 10
  • [ 63071-12-5 ]
  • [ 156094-63-2 ]
Reference: [1] Patent: WO2011/79076, 2011, A1, . Location in patent: Page/Page column 93
[2] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 577; 578
  • 11
  • [ 63071-12-5 ]
  • [ 623942-84-7 ]
Reference: [1] Patent: WO2011/28395, 2011, A1, . Location in patent: Page/Page column 20-21
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