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[ CAS No. 60588-81-0 ] {[proInfo.proName]}

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Chemical Structure| 60588-81-0
Chemical Structure| 60588-81-0
Structure of 60588-81-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 60588-81-0 ]

CAS No. :60588-81-0 MDL No. :MFCD11110226
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :VCJIRTWLMWNXEA-UHFFFAOYSA-N
M.W :143.57 Pubchem ID :10486967
Synonyms :

Calculated chemistry of [ 60588-81-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.37
TPSA : 33.12 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) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 0.63
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.55
Solubility : 4.01 mg/ml ; 0.0279 mol/l
Class : Very soluble
Log S (Ali) : -0.9
Solubility : 18.1 mg/ml ; 0.126 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.514 mg/ml ; 0.00358 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 60588-81-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60588-81-0 ]

* 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 [ 60588-81-0 ]
  • Downstream synthetic route of [ 60588-81-0 ]

[ 60588-81-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 57266-69-0 ]
  • [ 60588-81-0 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With isopropyl chloroformate; triethylamine In tetrahydrofuran at 0 - 20℃; for 1 h;
Stage #2: at 20℃; for 2 h;
To a solution of 3-chloropyridine-2-carboxylic acid (2.1 g, 13.33 mmol, 1.00 equiv) in THF (40 mL) was added Et3N (2.7 g, 26.68 mmol, 2.00 equiv), followed by the addition of chloro(propan-2-yloxy)methanone (2.45 g, 19.99 mmol, 1.50 equiv) dropwise with stirring at 0° C.
The solution was strried for 1 h at room temperture.
The solid was removed by filtration.
To the filtrate was added NaBH4 (1.53 g, 40.44 mmol, 3.00 equiv).
The resulting solution was stirred for 2 h at rt, then diluted with 50 mL of H2O and extracted with 2*100 mL of EtOAc.
The combined organic layers were washed with 50 mL of saturated Nacl, dried over Na2SO4, concentrated under vacuum, and purified with silica gel chromatography using with EtOAc/petroleum ether (1:6) to afford 0.9 g (47percent) of the title compound as a colorless oil.
Reference: [1] Patent: US2018/162822, 2018, A1, . Location in patent: Paragraph 0606
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837
  • 2
  • [ 52378-63-9 ]
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Reference: [1] Patent: US4013769, 1977, A,
[2] Patent: US4025527, 1977, A,
[3] Patent: US4024260, 1977, A,
[4] Patent: US4056621, 1977, A,
  • 3
  • [ 626-60-8 ]
  • [ 68-12-2 ]
  • [ 60588-81-0 ]
Reference: [1] Patent: WO2005/9980, 2005, A1, . Location in patent: Page/Page column 50
  • 4
  • [ 38180-46-0 ]
  • [ 60588-81-0 ]
Reference: [1] Patent: US6387911, 2002, B1,
  • 5
  • [ 124425-86-1 ]
  • [ 60588-81-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
  • 6
  • [ 72093-03-9 ]
  • [ 60588-81-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837
  • 7
  • [ 52313-57-2 ]
  • [ 60588-81-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
  • 8
  • [ 60588-81-0 ]
  • [ 185315-53-1 ]
YieldReaction ConditionsOperation in experiment
69% With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3 h; Synthesis of 3-chloro-2-(chloromethvDpyridine (32 31 To a solution of compound 31 (300 mg, 2.1 mmol) in DCM (4 mL) was added DIE A (539 mg, 4.2 mmol) at 0 °C, then MsCl (263 mg, 2.3 mmol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 3h. Water was added, and the mixture was extracted with DCM, washed with sat. NaHCO and brine, dried over a?.S04, filtered, concentrated under reduced pressure to give compound 32 (240 mg, 69 percent) as a yellow oil.
Reference: [1] Patent: WO2015/143164, 2015, A1, . Location in patent: Page/Page column 119-120
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
  • 9
  • [ 60588-81-0 ]
  • [ 206181-90-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837
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