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[ CAS No. 65169-38-2 ] {[proInfo.proName]}

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Chemical Structure| 65169-38-2
Chemical Structure| 65169-38-2
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Product Details of [ 65169-38-2 ]

CAS No. :65169-38-2 MDL No. :MFCD07082888
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BXUFVXSRHLSIMN-UHFFFAOYSA-N
M.W : 152.58 Pubchem ID :12387736
Synonyms :

Calculated chemistry of [ 65169-38-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.93
TPSA : 36.68 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 0.73
Log Po/w (SILICOS-IT) : 2.4
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.571 mg/ml ; 0.00374 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 0.777 mg/ml ; 0.00509 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.122 mg/ml ; 0.0008 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 65169-38-2 ]

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 [ 65169-38-2 ]

* 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 [ 65169-38-2 ]
  • Downstream synthetic route of [ 65169-38-2 ]

[ 65169-38-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 71493-72-6 ]
  • [ 65169-38-2 ]
YieldReaction ConditionsOperation in experiment
85% at 50 - 55℃; for 2 h; 1. After enamine formation was complete as above in Step 1 B, HC1 gas was slowly charged at room temperature while stirring. After charging was completed the reaction mixture was heated to 50-55°C and held until the reaction was complete. Completion was checked by HPLC.2. If the reaction was not complete, step 1 was repeated. The reaction was typically complete in about 2 hours.3. After completion of reaction, the reaction mixture was distilled to remove approximately 75percent of solvent, followed by the addition of water (150-200ml) to the residue with stirring.4. The product was filtered and washed with water (3xSOml). 5. The product was dried at around 3 0-40°C under vacuum to a constant weight. The average telescope yield for the three steps (Steps lA, lB and 1C) is 85percent. The purity was 98Apercent by HPLC.
Reference: [1] Patent: WO2016/118586, 2016, A1, . Location in patent: Page/Page column 23; 24
[2] Patent: WO2015/31718, 2015, A1, . Location in patent: Paragraph 0048-0053
[3] Green Chemistry, 2017, vol. 19, # 13, p. 2986 - 2991
  • 2
  • [ 93271-59-1 ]
  • [ 65169-38-2 ]
YieldReaction ConditionsOperation in experiment
98.2% With phosphorus pentachloride In water (c)
Preparation of 2-chloro-3-cyano-4-methylpyridine (Chlorination)
The product of the preceding step, 4-methyl-3-cyano-2-pyridone (40.7 g, 0.304 moles) was added to a stirred solution of POCL3 (140 g, 0.912 moles) and PCl5 (19.0 g, 0.091 moles).
The reaction was heated to reflux (approximately 115° C.) and held under those conditions for two hours.
Excess POCL3 was removed by distillation.
The reaction mixture was then cooled followed by the addition of water (30 mL) water.
The aqueous mixture was extracted with 30 mL methylene chloride.
The extracts were concentrated and 43.2 g was recovered as a tan solid, which was determined to be 2-chloro-3-cyano-4-methylpyridine (4).
mp: 102-104° C.
Yield: 98.2percent
1H NMR: 8.03 (d, J=2 Hz, 1H), 7.6 (d, J=2 Hz, 1H), 2.5 (s, 3H); 13C NMR 156.1, 152.6, 151.8, 124.9, 114.4, 111.8, 20.6
Mass spectrum m/z: 155, 154, 152, 117, 116, 90, 89, 76, 64, 63, 62
FTIR (KBr): 3144, 2979, 2834, 2228, 1653, 1616, 1540, 1484, 1242, 1218, 1173, 819, 607 cm-1
Reference: [1] Patent: US2002/52507, 2002, A1,
[2] Patent: EP1679003, 2006, A1, . Location in patent: Page/Page column 22
  • 3
  • [ 93271-59-1 ]
  • [ 65169-38-2 ]
YieldReaction ConditionsOperation in experiment
89.2% for 1 h; Heating / reflux Example 9 Synthesis of 2-chloro-4-methylpyridine-3-carbonitrile (9)
To a 250 ML flask equipped with a magnetic stirrer was added 10g of 2-hydroxy-4-methyl-3-pyridinylcarbonitrile (8) and 60 ML of phosphorous oxychloride..
The mixture was refluxed for one hour..
The excess POCl3 was distilled under reduced pressure..
The residue was poured into water..
The crystalline material was filtered and dried at to give 10.2g (89.2percent) of (9)..
m.p.: 109-110°C, NMR (DMSO); ppm: 2.56 (s,3H); 7.6 (bs,1H); 8.56 (m,1H).
MS: (EI) m/z M+ 152, 146
88% for 2 h; Reflux A mixture of 2-hydroxy-4-methylpyridine-3-carbonitrile (3.0 g, 22.38 mmol; obtained as described in WO 2011/088201), phosphoryl chloride (6.26 mL, 67.16 mmol) and phosphorus pentachloride (1.4 g, 6.71 mmol) was refluxed for 2 hours. The reaction mixture was cooled to room temperature, and then concentrated under vacuo to dryness. The obtained residue was diluted with aqueous sodium bicarbonate solution. The precipitate thus obtained was collected by filtration and dried to give the title compound as an off-white solid (3.0 g, 88percent). MS(ESI)m/z: 153.1 (M+l) ; 1H NMR CDC13: δ 8.43 (d, J = 5.2 Hz, 1H), 7.22 (d, J = 4.8 Hz, 1H) , 2.8 ( s, 3H
Reference: [1] Patent: EP1064265, 2004, B1, . Location in patent: Page 5
[2] Patent: WO2016/21742, 2016, A1, . Location in patent: Paragraph 0244; 0245
[3] Patent: US6111112, 2000, A,
[4] Research on Chemical Intermediates, 2011, vol. 37, # 6, p. 599 - 604
  • 4
  • [ 67-56-1 ]
  • [ 41125-09-1 ]
  • [ 109-77-3 ]
  • [ 65169-38-2 ]
YieldReaction ConditionsOperation in experiment
180.1 g
Stage #1: at 20℃; for 4 h;
Stage #2: at 20℃; for 5 h;
Stage #3: With hydrogenchloride In isopropyl alcohol at 10℃; for 10 h; Cooling with ice
Under ice-cooling, add to the reaction flask30percent by weight of hydrogen chloride in isopropanol 1.2 L,The reddish brown oil obtained in Example 1 was slowly added,After completion of the addition, hydrogen chloride gas was continuously introduced at 10 ° C,Keep the reaction for 10 hours;The reaction mixture was added dropwise to 6 L of water,Keeping stirring for 1 hour; filtering,The filter cake was washed with ice water, dried in vacuo,To obtain 180.1 g of 2-chloro-3-cyano-4-methylpyridine, and the HPLC purity was 99.8percent.
Reference: [1] Patent: CN105859614, 2016, A, . Location in patent: Paragraph 0045; 0051
  • 5
  • [ 875-35-4 ]
  • [ 65169-38-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697
  • 6
  • [ 13166-10-4 ]
  • [ 65169-38-2 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 20, p. 5298 - 5301
[2] Patent: WO2015/31718, 2015, A1,
[3] Patent: WO2016/118586, 2016, A1,
[4] Green Chemistry, 2017, vol. 19, # 13, p. 2986 - 2991
  • 7
  • [ 5444-02-0 ]
  • [ 65169-38-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697
  • 8
  • [ 65169-38-2 ]
  • [ 133627-45-9 ]
Reference: [1] Research on Chemical Intermediates, 2011, vol. 37, # 6, p. 599 - 604
[2] Patent: WO2016/118586, 2016, A1,
[3] Green Chemistry, 2017, vol. 19, # 13, p. 2986 - 2991
  • 9
  • [ 65169-38-2 ]
  • [ 133627-47-1 ]
Reference: [1] Patent: WO2016/118586, 2016, A1,
[2] Green Chemistry, 2017, vol. 19, # 13, p. 2986 - 2991
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