Home Cart 0 Sign in  
X

[ CAS No. 112197-16-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 112197-16-7
Chemical Structure| 112197-16-7
Chemical Structure| 112197-16-7
Structure of 112197-16-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 112197-16-7 ]

Related Doc. of [ 112197-16-7 ]

Alternatived Products of [ 112197-16-7 ]

Product Details of [ 112197-16-7 ]

CAS No. :112197-16-7 MDL No. :MFCD09880283
Formula : C7H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OFWONXXWLCHTSR-UHFFFAOYSA-N
M.W :139.15 Pubchem ID :10630565
Synonyms :

Calculated chemistry of [ 112197-16-7 ]

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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 0.27
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.18
Solubility : 9.09 mg/ml ; 0.0653 mol/l
Class : Very soluble
Log S (Ali) : -0.72
Solubility : 26.5 mg/ml ; 0.19 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 : 1.47

Safety of [ 112197-16-7 ]

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 [ 112197-16-7 ]

* 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 [ 112197-16-7 ]
  • Downstream synthetic route of [ 112197-16-7 ]

[ 112197-16-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 67367-26-4 ]
  • [ 112197-16-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium borohydride In tetrahydrofuran at 70℃; for 2 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
Example 138: Preparation of |"2-methoxy-pyridin-3-vπ-methanolTo a solution of 2-methoxy-pyridine-3-carboxylic acid methyl ester (1.021 g, 6.11 mmol) (Example 137) in anhydrous tetrahydrofuran (5 ml) was added in portions lithium borohydride (0.266 g, 1.22 mmol). The reaction mixture was heated to 700C for 2 hours. The reaction mixture was quenched by addition of aqueous ammonium chloride (saturated) and then extracted three times with ethyl acetate (3x 20 ml). The combined organic extracts were dried over magnesium sulfate and concentrated to give [2- methoxy-pyridin-3-yl]-rnethanol as a colourless oil (0.849 g, 100percent yield). 1H-NMR (400 MHz, CDCl3): 2.29 (IH, m, OH), 4.0 (3H5 s, Me), 4.67 (2H, m, CH2), 6.89 (IH, m, CH), 7.59 (IH, m, CH), 8.1 (IH, m, CH) ppm.
81%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3.66667 h;
Stage #2: With water; Rochelle's salt In tetrahydrofuran at 20℃; for 0.416667 h;
Step 2:
(2-Methoxy-pyridin-3-yl)-methanol
A solution of 2-methoxy-nicotinic acid methyl ester (4.42 g, 26.5 mmol) in tetrahydrofuran (7 mL) was added via an addition funnel over a period of 15-20 min to a cooled (0° C.) mixture of lithium aluminum hydride (1.22 g, 32.1mmol) in tetrahydrofuran (20 mL).
The mixture was stirred at 0° C. for 40 min and then at room temperature for 3 h.
The reaction mixture was poured into a solution of potassium sodium tartrate (10percent w/v) and the resulting mixture was stirred at room temperature for 25 min.
The mixture was filtered through a pad of Celite, washing with ethyl acetate (400 mL).
The organic layer of the filtrate was separated and the aqueous layer was extracted with ethyl acetate (2*100 mL).
The combined organic layers were washed with brine (100 mL), dried (magnesium sulfate), filtered and purified using a Biotage 40M system, eluding with 30percent ethyl acetate/hexanes, to give (2-methoxy-pyridin-3-yl)-methanol (2.97 g, 81percent) as a white solid.
Reference: [1] Patent: WO2007/71900, 2007, A1, . Location in patent: Page/Page column 95
[2] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
[3] Patent: US2007/49632, 2007, A1, . Location in patent: Page/Page column 38
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 18, p. 3386 - 3399
[5] Patent: EP1422228, 2004, A1, . Location in patent: Page 205-206
[6] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
  • 2
  • [ 71255-09-9 ]
  • [ 112197-16-7 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 1 h; Step 1: (2-Methoxypyridin-3-yl)methanoI To a solution of 2-methoxy-pyridine-3-carbaldehyde (2.03 g, 14.8 mmol) in THF (35 mL) was added sodium tetrahydroborate (617 mg, 16.3 mmol) at rt and the mixture was stirred for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na S04 and concentrated. The crude product was purified on silica gel to give (2- methoxypyridin-3-yl)methanol (2.05 g, 99percent) as a clear oil. LCMS (FA): m/z = 140 (M+H).
94% With sodium tetrahydroborate In ethanol at -40℃; for 0.75 h; Inert atmosphere Sodium borohydride (0.17 g, 4.5 mmol) was dissolved in 20 ml ethanol under argon and the mixture cooled to -40 °C in a cryo-cool.
A solution of 2-methoxynicotinaldehyde (2.0 g, 14.6 mmol) dissolved in 4 ml ethanol was added drop-wise and with stirring.
The mixture was stirred at -40 °C for 45 min. 10 ml Brine was added carefully and the mixture was then allowed to warm to room temperature.
The organics were evaporated under reduced pressure.
The mixture was partitioned between ethyl acetate and water.
The aqueous phase was extracted with ethyl acetate and the combined organics were dried over magnesium sulphate, filtered and evaporated to give 44 (1.90 g, 13.7 mmol, 94percent yield) as a pale yellow oil.
Purity 100percent. 1H NMR (300 MHz, CDCl3) δ ppm 2.30 (t, J = 6.5 Hz, 1H, OH), 4.00 (s, 3H, MeO), 4.66 (d, J = 6.3 Hz, 2H, CH2), 6.90 (dd, J = 5.0, 7.1 Hz, 1H, H-5), 7.58 (d, J = 7.1 Hz, 1H, H-4), 8.11 (d, J = 4.9 Hz, 1H, H-6). UPLC/MS (3 min) retention time 0.77 min. LRMS: m/z 140 (M+1).
Reference: [1] Patent: WO2015/2994, 2015, A2, . Location in patent: Paragraph 00194
[2] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 102 - 133
[3] Patent: US2008/103129, 2008, A1, . Location in patent: Page/Page column 47
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 405 - 408
  • 3
  • [ 50-00-0 ]
  • [ 163105-90-6 ]
  • [ 112197-16-7 ]
YieldReaction ConditionsOperation in experiment
84% With bis(η3-allyl-μ-chloropalladium(II)); 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride In tetrahydrofuran; water at 100℃; for 2 h; Inert atmosphere; Sealed tube General procedure: [PdCl(η3-allyl)]2 (0.00125-0.005 mmol), imidazolinium salt 1a (0.0025-0.01 mmol), arylboronic acid (0.50 mmol) and an inorganic base (2.0 mmol) were charged in a 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (0.5 mL) and 37 wt percent formaldehyde in H2O (102 mg, formaldehyde 1.25 mmol) were added via the rubber septum with syringe. In anargon flow, the rubber septum was replaced with a Teflon liners crew cap. The test tube was placed in an oil bath preheated at 100 C. The reaction mixture was stirred for 2 h and was cooled to room temperature. Then, operation of (i) or (ii) was performed. (i)The obtained crude was purified by passing it through a silica gel column with a hexane/ethyl acetate eluent (Table 4 entry 2 and Table 5 entries 8-16). (ii) Diphenylmethane (84.1 mg, 0.50 mmol) as an internal standard was added and then an aliquot of the organic layer of the reaction mixture was subjected to the quantitative analysis by 1H NMR (Table 4).
Reference: [1] Tetrahedron, 2014, vol. 71, # 1, p. 19 - 26
  • 4
  • [ 16498-81-0 ]
  • [ 112197-16-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 18, p. 3386 - 3399
[2] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 571; 572
  • 5
  • [ 49609-84-9 ]
  • [ 112197-16-7 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 6
  • [ 2942-59-8 ]
  • [ 112197-16-7 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 7
  • [ 40134-18-7 ]
  • [ 112197-16-7 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 8
  • [ 110-88-3 ]
  • [ 1628-89-3 ]
  • [ 112197-16-7 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1367 - 1371
  • 9
  • [ 112197-16-7 ]
  • [ 942060-13-1 ]
YieldReaction ConditionsOperation in experiment
70% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 2 h; Step 2: 3-(Bromomethyl)-2-methoxypyridine Int-37 To a solution of (2-methoxypyridin-3-yl)methanol (811 mg, 5.8 mmol) and N- bromosuccinimide (1.24 g, 7.0 mmol) in DCM (10 mL) was added triphenylphosphine (1.8 g, 7.0 mmol) at rt and the mixture was stirred for 2 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2S04 and concentrated. The crude product was purified on silica gel to give 3-(bromomethyl)-2-methoxypyridine (829 mg, 70percent) as clear oil. FontWeight="Bold" FontSize="10" H NMR (CDC13) 8.14 (dd, J= 5.0, 1.9 Hz, 1H), 7.63 (dd, J- 7.3, 1.9 Hz, 1H), 6.89 (dd, J= 7.3, 5.0 Hz, 1H), 4.51 (s, 2H), 4.04 (s, 3H).
42% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 16 h; Example 139: Preparation of 3-bromomethyl-2-methoxy-pyridineTo a solution of [2-methoxy-pyridin-3-yl]-methanol (0.849 g, 6.11 mmol) (Example 138) in dichloromethane (30 ml) was added sequentially triphenyl phosphine (1.683 g, 6.42 mmol) and carbon tetrabromide (1.904 g, 5.81 mmol). The reaction mixture was stored at room temperature for 16 hours. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel (eluent: 0- 25percent ethyl acetate in hexane) to give 3-bromomethyl-2-methoxy-pyridine as a colourless oil (0.511 g, 42percent yield). 'H-NMR (400 MHz, CDCl3): 4.02 (3H, s, Me), 4.5 (2H, m, CH2), 6.88 (IH, m, CH), 7.61 (IH, m, CH), 8.12 (IH, m, CH) ppm.
Reference: [1] Patent: WO2015/2994, 2015, A2, . Location in patent: Paragraph 00195
[2] Patent: WO2007/71900, 2007, A1, . Location in patent: Page/Page column 95
[3] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 571; 572
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 112197-16-7 ]

Ethers

Chemical Structure| 19230-59-2

[ 19230-59-2 ]

2-Methoxy-3-methylpyridine

Similarity: 0.96

Chemical Structure| 354824-19-4

[ 354824-19-4 ]

(2-Methoxypyridin-3-yl)methanamine

Similarity: 0.85

Chemical Structure| 942060-13-1

[ 942060-13-1 ]

3-(Bromomethyl)-2-methoxypyridine

Similarity: 0.84

Chemical Structure| 1196145-21-7

[ 1196145-21-7 ]

3-Ethynyl-2-methoxypyridine

Similarity: 0.82

Chemical Structure| 874822-98-7

[ 874822-98-7 ]

(5-Fluoro-2-methoxypyridin-3-yl)methanol

Similarity: 0.81

Alcohols

Chemical Structure| 91914-04-4

[ 91914-04-4 ]

3-Methylpyridin-2-ol

Similarity: 0.83

Chemical Structure| 1802489-60-6

[ 1802489-60-6 ]

(6-Bromo-2-methoxypyridin-3-yl)methanol

Similarity: 0.81

Chemical Structure| 874822-98-7

[ 874822-98-7 ]

(5-Fluoro-2-methoxypyridin-3-yl)methanol

Similarity: 0.81

Chemical Structure| 123148-66-3

[ 123148-66-3 ]

(2-Methoxypyridin-4-yl)methanol

Similarity: 0.81

Chemical Structure| 66080-45-3

[ 66080-45-3 ]

2-Methoxypyridin-4-ol

Similarity: 0.72

Related Parent Nucleus of
[ 112197-16-7 ]

Pyridines

Chemical Structure| 19230-59-2

[ 19230-59-2 ]

2-Methoxy-3-methylpyridine

Similarity: 0.96

Chemical Structure| 354824-19-4

[ 354824-19-4 ]

(2-Methoxypyridin-3-yl)methanamine

Similarity: 0.85

Chemical Structure| 942060-13-1

[ 942060-13-1 ]

3-(Bromomethyl)-2-methoxypyridine

Similarity: 0.84

Chemical Structure| 91914-04-4

[ 91914-04-4 ]

3-Methylpyridin-2-ol

Similarity: 0.83

Chemical Structure| 1196145-21-7

[ 1196145-21-7 ]

3-Ethynyl-2-methoxypyridine

Similarity: 0.82