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[ CAS No. 1121-76-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1121-76-2
Chemical Structure| 1121-76-2
Chemical Structure| 1121-76-2
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Product Details of [ 1121-76-2 ]

CAS No. :1121-76-2 MDL No. :MFCD00047425
Formula : C5H4ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :DPJVRASYWYOFSJ-UHFFFAOYSA-N
M.W : 129.54 Pubchem ID :70724
Synonyms :

Calculated chemistry of [ 1121-76-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.61
TPSA : 25.46 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) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : -0.44
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 0.79
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.92
Solubility : 15.5 mg/ml ; 0.12 mol/l
Class : Very soluble
Log S (Ali) : 0.37
Solubility : 304.0 mg/ml ; 2.35 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.21
Solubility : 8.04 mg/ml ; 0.0621 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 1121-76-2 ]

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 [ 1121-76-2 ]

* 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 [ 1121-76-2 ]
  • Downstream synthetic route of [ 1121-76-2 ]

[ 1121-76-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1121-76-2 ]
  • [ 420-37-1 ]
  • [ 63071-10-3 ]
YieldReaction ConditionsOperation in experiment
43%
Stage #1: at 20℃; for 2 h;
Stage #2: With ammonium peroxodisulfate In methanol; water for 1 h; Heating / reflux
4-Chloro-2-(hydroxymethyl)pyridine : A solution of 4-CHLOROPYRIDINE ASOXIDE (5 G, 38.6 MMOL) and TRIMETHYLOXONIUM TETRAFLUOROBORATE (5.94 G, 40.1 MMOI) in CH2CL2 (115 mL) was stirred for two hours at ambient temperature. The solvent was evaporated and the residue taken up in MeOH (115 mL) and heated to near boiling. Ammonium persulfate (1.76 G, 7.72 MMOL) dissolved in H2O (7.7 mL) was added and the mixture was heated to reflux for 30 min. A second portion of ammonium persulfate (0.88 G) in H2O (3.9 mL) was added and the mixture was refluxed for another 30 min. The solvent was evaporated and the residue was partitioned between CHZCTZ and aqueous Na2CO3 (10percent w/v). The organic layer was washed with H2O, dried over MgSO4 and evaporated leaving 2.4 G (43percent) of the title compound. 1H NMR (CDC13) 8 8.20 (d, 1H, J=5. 0 Hz, H-6); 7.31 (s, 1H, H-3); 7.04 (d, 1H, J=5. 0 Hz, H-5); 5.46 (s, LH, OH); 4.61 (s, 2H, CH2).
Reference: [1] Patent: WO2005/12323, 2005, A2, . Location in patent: Page/Page column 46
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[3] Patent: EP1422228, 2004, A1, . Location in patent: Page 199
  • 2
  • [ 1121-76-2 ]
  • [ 63071-10-3 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 317 - 326
  • 3
  • [ 1121-76-2 ]
  • [ 22282-65-1 ]
Reference: [1] Patent: WO2005/12323, 2005, A2,
  • 4
  • [ 1121-76-2 ]
  • [ 19798-80-2 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 12, p. 4554 - 4557
[2] Bioorganic and medicinal chemistry letters, 2000, vol. 10, # 17, p. 1975 - 1978
[3] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 465 - 472
  • 5
  • [ 1121-76-2 ]
  • [ 7677-24-9 ]
  • [ 19235-89-3 ]
YieldReaction ConditionsOperation in experiment
99% With N,N-Dimethylcarbamoyl chloride In acetonitrile at 20℃; for 18 h; Reference Example 110
4-Chloro-2-cyanopyridine
4-Chloropyridine N-oxide (7.53 g, 58.1 mmol) and N,N-dimethylcarbamoyl chloride (9.36 g, 87.0 mmol) were added to acetonitrile (200 ml), and trimethylsilyl cyanide (11.5 g, 116 mmol) was added dropwise thereto..
The mixture was stirred at room temperature for 18 hrs..
The reaction mixture was combined with ethyl acetate and water..
The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over magnesium sulfate..
The solvent was evaporated, and the residue was subjected to a silica gel (200 g) column chromatography..
The fractions eluted with n-hexane-ethyl acetate (3:1, v/v) were collected, concentrated to give the titled compound (8.05 g, 99 percent) as a pale yellow oil.1H-NMR (CDCl3) δ: 7.54-7.56 (1H, m), 7.72(1H, s), 8.63 (1H, d, J = 5.3 Hz). IR(KBr): 2239, 1568, 1549, 1462, 1379, 1288, 1215, 844, 704 cm-1.
87% With triethylamine In acetonitrile for 48 h; Heating / reflux To a solution of 4-chloropyridine N-oxide (5.0 g, 38.6 mmol) in CAN (100 mL) was added trimethylsilyl cyanide (7.7 g, 77.2 mmol) and TEA (8.1 mL, 57.9 mmol).
The solution was heated at reflux for 48 h.
The reaction was then concentrated and diluted with DCM and water before adding 1N HCl[(caution]).
The mixture was extracted with DCM and the organic solutions were combined and washed with brine, dried over Na2SO4 and concentrated to yield the title compound as a brown solid (4.62 g, 87percent).
1H NMR (300 MHz, d6-DMSO) δ: 8.67 (dd, J1=0.57 Hz, J2=5.5 Hz, 1H), 8.29 (dd, J=0.75 Hz, J2=2.1, 1H), and 7.88 (dd, J1=0.2.1 Hz, J2=5.5 m, 1H).
Reference: [1] Patent: EP1424336, 2004, A1, . Location in patent: Page 219
[2] Patent: US2006/160803, 2006, A1, . Location in patent: Page/Page column 146
[3] Tetrahedron Asymmetry, 2005, vol. 16, # 20, p. 3427 - 3435
[4] Patent: WO2005/95326, 2005, A2, . Location in patent: Page/Page column 225-226
[5] Patent: WO2005/87215, 2005, A1, . Location in patent: Page/Page column 143
[6] Advanced Functional Materials, 2013, vol. 23, # 18, p. 2285 - 2294
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 5072 - 5085
  • 6
  • [ 1121-76-2 ]
  • [ 79-44-7 ]
  • [ 19235-89-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In dichloromethane To a mixture of 4-chloropyridine-N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cycanide (4.84 g, 46.3 mmol) in dichloromethane (60 ml) cooled to 0° C. was added dropwise N,N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol).
The mixture was allowed to warm to ambient temperature and stirred for 16 h.
The mixture was cooled to 0° C. and a 30percent aqueous solution of potassium carbonate (100 ml) was added.
The crude product was extracted with dichloromethane (100 ml*2), the organic extracts dried (MgSO4) and evaporated to give 4-chloro-2-pyridinecarbonitrile (5.35 g, 100percent).
1H-NMR (CDCl3) δ: 8.63 (1H, d, J=4.8 Hz), 7.72 (1H, d, J=2.6 Hz), 7.55 (1H, dd, J=1.8, 5.1 Hz).
100% With potassium carbonate In dichloromethane To a mixture of 4-chloropyridine-N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cycanide (4.84 g, 46.3 mmol) in dichloromethane (60 ml) cooled to 0 °C was added dropwise N,N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol).
The mixture was allowed to warm to ambient temperature and stirred for 16 h.
The mixture was cooled to 0 °C and a 30percent aqueous solution of potassium carbonate (100 ml) was added.
The crude product was extracted with dichloromethane (100 ml x 2), the organic extracts dried (MgSO4) and evaporated to give 4-chloro-2-pyridinecarbonitrile (5.35 g, 100percent).
1H-NMR (CDCl3) 8.63 (1 H, d, J=4.8 Hz), 7.72 (1 H, d, J=2.6 Hz), 7.55 (1 H, dd, J=1.8, 5.1 Hz).
Reference: [1] Patent: US6608070, 2003, B1,
[2] Patent: EP1065206, 2001, A1,
  • 7
  • [ 1121-76-2 ]
  • [ 77-78-1 ]
  • [ 19235-89-3 ]
Reference: [1] Patent: US5219847, 1993, A,
  • 8
  • [ 1121-76-2 ]
  • [ 151-50-8 ]
  • [ 19235-89-3 ]
Reference: [1] Heterocycles, 2000, vol. 53, # 4, p. 797 - 804
  • 9
  • [ 1121-76-2 ]
  • [ 99586-65-9 ]
Reference: [1] Heterocycles, 2000, vol. 53, # 4, p. 797 - 804
  • 10
  • [ 1121-76-2 ]
  • [ 62-53-3 ]
  • [ 22961-45-1 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 2404,2407
  • 11
  • [ 1121-76-2 ]
  • [ 98-80-6 ]
  • [ 1131-61-9 ]
Reference: [1] Synlett, 1999, # 1, p. 45 - 48
  • 12
  • [ 1121-76-2 ]
  • [ 100-58-3 ]
  • [ 1131-61-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 20, p. 5312 - 5315
  • 13
  • [ 109-04-6 ]
  • [ 1121-76-2 ]
  • [ 14162-94-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 9, p. 2310 - 2313
  • 14
  • [ 1121-76-2 ]
  • [ 60159-37-7 ]
Reference: [1] Tetrahedron Asymmetry, 2005, vol. 16, # 20, p. 3427 - 3435
  • 15
  • [ 1121-76-2 ]
  • [ 896139-36-9 ]
Reference: [1] Tetrahedron Asymmetry, 2005, vol. 16, # 20, p. 3427 - 3435
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