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[ CAS No. 95652-81-6 ] {[proInfo.proName]}

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Chemical Structure| 95652-81-6
Chemical Structure| 95652-81-6
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Product Details of [ 95652-81-6 ]

CAS No. :95652-81-6 MDL No. :MFCD11847276
Formula : C7H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AVBARORPQMEWPR-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :10855945
Synonyms :

Calculated chemistry of [ 95652-81-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.13
TPSA : 39.19 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.52
Log Po/w (SILICOS-IT) : 2.12
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.16 mg/ml ; 0.00675 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.66 mg/ml ; 0.00969 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.333 mg/ml ; 0.00194 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 95652-81-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 95652-81-6 ]

* 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 [ 95652-81-6 ]
  • Downstream synthetic route of [ 95652-81-6 ]

[ 95652-81-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 124-41-4 ]
  • [ 69045-78-9 ]
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  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
  • 2
  • [ 95652-81-6 ]
  • [ 65515-33-5 ]
Reference: [1] Patent: WO2012/110860, 2012, A1, . Location in patent: Page/Page column 83
  • 3
  • [ 38496-18-3 ]
  • [ 124-41-4 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Patent: WO2013/130689, 2013, A1, . Location in patent: Paragraph 00931; 00932; 00933; 00934
  • 4
  • [ 2591-86-8 ]
  • [ 17228-64-7 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56
  • 5
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
  • 6
  • [ 17228-64-7 ]
  • [ 68-12-2 ]
  • [ 95652-81-6 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78℃; for 2 h;
To a solution of 2-chloro-6-methoxypyridine (5 g, 34.82 mmol) in THF (100 mL), cooled to −78° C. was added tBuLi (1.7 M) (18.5 mL, 31.34 mmol) and stirred for 1 h; DMF (92.2 g, 31.34 mmol) was then added at −78° C. and stirred for 2 h. The reaction mixture was quenched with acetic acid and poured in to ice cold water, basified with sat NaHCO3 and extracted with EtOAc (2×500 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to get crude product, which was purified by silica gel column (eluting with pet ether: ethyl acetate=10:1) to afford 6-chloro-2-methoxynicotinaldehyde as an off white solid (3.8 g, 65percent). ES+, m/z 172 [M+H]; [C7H6ClNO2], 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 8.07 (d, J=8.04 Hz, 1H), 7.03 (d, J=8.04 Hz, 1H), 3.79 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5857 - 5867
[2] Patent: US2018/65917, 2018, A1, . Location in patent: Paragraph 0209
[3] Patent: EP1405859, 2004, A1, . Location in patent: Page 23
[4] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[5] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732
  • 7
  • [ 17228-64-7 ]
  • [ 95652-81-6 ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butyl lithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; acetic acid; pentane EXAMPLE 1
6-Chloro-2-methoxy-3-pyridinecarboxaldehyde
To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min.
The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperature for 1.5 h.
After the addition of glacial acetic acid (8.6 mL, 150 mmol), the reaction mixture was allowed to warm to room temperature over a 30- min period, then diluted with ether (200 mL).
The organic phase was washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL), and was dried over MgSO4.
Concentration afforded the crude product as a light yellow solid which was recrystallized from hexanes to give 9.6 g (75percent) of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde as a white solid: mp 80°-81° C. (mp 62°-64° C.) (See Dainter, R. S.; Suschitzky, H.; Wakefield, B. J. Tetrahedron Lett. 1984, 25, 5693.).
1 H NMR (300 MHz, CDCl3) δ 10.31 (s,1H), 8.07 (d, 1H, J=9 Hz), 7.03 (d, 1H, J=9 Hz), 4.09 (s, 3H); IR (nujol) 1685, 1580, 1565, 1270, 1140, 1090, 1005, 905, 820, 755 cm-1.
75% With tert.-butyl lithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; acetic acid; pentane EXAMPLE 1
6-Chloro-2-methoxy-3-pyridinecarboxaldehyde
To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min.
The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperature for 1.5 h.
After the addition of glacial acetic acid (8.6 mL, 150 mmol), the reaction mixture was allowed to warm to room temperature over a 30- min period, then diluted with ether (200 mL).
The organic phase was washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL), and was dried over MgSO4.
Concentration afforded the crude product as a light yellow solid which was recrystallized from hexanes to give 9.6 g (75percent) of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde as a white solid: mp 80°-81° C. (mp 62°-64° C.)(See Dainter, R. S.; Suschitzky, H.; Wakefield, B. J. Tetrahedron Lett. 1984, 25, 5693.).
1 H NMR (300 MHz, CDCl3) δ 10.31 (s, 1H), 8.07 (d, 1H, J=9 Hz), 7.03 (d, 1H, J=9 Hz), 4.09 (s, 3H); IR (nujol) 1685, 1580, 1565, 1270, 1140, 1090, 1005, 905, 820, 755 cm-1.
Reference: [1] Patent: US5212317, 1993, A,
[2] Patent: US5162532, 1992, A,
[3] Patent: WO2012/110860, 2012, A1, . Location in patent: Page/Page column 82-83
  • 8
  • [ 55304-73-9 ]
  • [ 124-41-4 ]
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YieldReaction ConditionsOperation in experiment
71.3% at 55℃; for 3 h; 2,6-Dichloronicotinaldehyde (1 g, 5.68 mmol) was diluted with sodium methoxide (11.4 mL, 5.68 mmol) (solution in methanol) and heated to 55°C. After stirring for 3 hours, the reaction was loaded directly onto a silica gel column and eluted with 5percent ethyl acetate/hexanes to 50percent ethyl acetate/hexanes to yield 6-chloro-2- methoxynicotinaldehyde (0.695 g, 4.05 mmol, 71.3 percent yield).
Reference: [1] Patent: WO2010/75200, 2010, A1, . Location in patent: Page/Page column 164
  • 9
  • [ 38496-18-3 ]
  • [ 124-41-4 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Patent: WO2013/130689, 2013, A1, . Location in patent: Paragraph 00931; 00932; 00933; 00934
  • 10
  • [ 67-56-1 ]
  • [ 55304-73-9 ]
  • [ 95652-81-6 ]
Reference: [1] Synthesis, 2005, # 16, p. 2751 - 2757
  • 11
  • [ 2402-78-0 ]
  • [ 95652-81-6 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[2] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732
  • 12
  • [ 67-56-1 ]
  • [ 69045-78-9 ]
  • [ 26218-80-4 ]
  • [ 95652-81-6 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 49, p. 5693 - 5696
  • 13
  • [ 124-41-4 ]
  • [ 69045-78-9 ]
  • [ 66572-55-2 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
  • 14
  • [ 2591-86-8 ]
  • [ 17228-64-7 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56
  • 15
  • [ 124-41-4 ]
  • [ 40381-90-6 ]
  • [ 95652-80-5 ]
  • [ 95652-81-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
[2] Journal of the Chemical Society, Perkin Transactions 1, 1989, # 2, p. 283 - 287
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