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[ CAS No. 60290-21-3 ] {[proInfo.proName]}

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Chemical Structure| 60290-21-3
Chemical Structure| 60290-21-3
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Product Details of [ 60290-21-3 ]

CAS No. :60290-21-3 MDL No. :MFCD07781160
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 152.58 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 60290-21-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.1
TPSA : 28.68 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) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.323 mg/ml ; 0.00212 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.04 mg/ml ; 0.00681 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.0472 mg/ml ; 0.000309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 60290-21-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60290-21-3 ]

* 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 [ 60290-21-3 ]
  • Downstream synthetic route of [ 60290-21-3 ]

[ 60290-21-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 494767-29-2 ]
  • [ 60290-21-3 ]
YieldReaction ConditionsOperation in experiment
91% With manganese(IV) oxide In tetrahydrofuranHeating / reflux Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3No.2-c]pyridine; [00124] To a solution of the amine (2.18 g, 14.2 mmol) in THF (60 mL) was added Mnψ2 (7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 h, a further portion of MnO2 (3 g, 34.5 mmol) was added and stirring continued overnight. The reaction was filtered through Celite and concentrated to give a white solid (1.95 g, 91percent) .[00125] The indole (1.48 g, 9.72 mmol) was dissolved in CH2C12 (50 mL) and cooled to 0 aC under nitrogen. N- Bromosuccinimide (1.82 g, 10.2 mmol) was added and after 30 min the ice-bath was removed and stirring continued for a further 30 min. The desired bromide (1.53 g, 68percent) was filtered off and dried on high vacuum. MS (ES+) m/e = 231. IH NMR (DMSO) 7.48 (IH, d) , 7.80 (IH, s), 8.00 (lH, d) .
Reference: [1] Patent: WO2007/95223, 2007, A2, . Location in patent: Page/Page column 41
  • 2
  • [ 54415-77-9 ]
  • [ 60290-21-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 359 - 367
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3199 - 3203
  • 3
  • [ 271-34-1 ]
  • [ 60290-21-3 ]
Reference: [1] Patent: WO2017/23987, 2017, A1,
[2] Patent: WO2017/24003, 2017, A1,
[3] Patent: WO2017/24010, 2017, A1,
[4] Patent: WO2017/23984, 2017, A1,
  • 4
  • [ 109113-39-5 ]
  • [ 60290-21-3 ]
Reference: [1] Patent: WO2017/23987, 2017, A1,
[2] Patent: WO2017/24003, 2017, A1,
[3] Patent: WO2017/24010, 2017, A1,
[4] Patent: WO2017/23984, 2017, A1,
  • 5
  • [ 26956-47-8 ]
  • [ 60290-21-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 359 - 367
  • 6
  • [ 557-21-1 ]
  • [ 60290-21-3 ]
  • [ 1040682-68-5 ]
YieldReaction ConditionsOperation in experiment
32% With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc In 1-methyl-pyrrolidin-2-one at 120℃; for 18 h; Inert atmosphere step 1 : A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61mmol), Pd2(dba)3 (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120 °C for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3 x 50 mL), dried (MgSO i), filtered and concentrated under reduced pressure. The crude residue was purified by S1O2 chromatography eluting with petroleum ethenEtOAc (1 :1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32 percent). MS (ESI) m/z: 144.3 [M+l] +.
11% With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc In 1-methyl-pyrrolidin-2-one at 120℃; for 18 h; Inert atmosphere A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (0.5 g, 3.28 mmol, 1.0 eq), Zn(CN)2 (422 mg, 3.61 mmol, 1.1 eq) , Pd2(dba)3 (600.0 mg, 0.656 mmol, 0.2 eq), dppf (729.0 mg, 1.312 mmol, 0.4 eq), Zn (21.0 mg, 0.328 mmol, 0.1 eq) in MP (30.0 mL) was stirred at 120 °C for 18 h under Ar. After the reaction was complete, the mixture was extracted with EA. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide lH-pyrrolo[3,2-c] pyridine-4-carbonitrile (68.0 mg, 11percent).
Reference: [1] Patent: WO2013/92940, 2013, A1, . Location in patent: Page/Page column 38; 39
[2] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00682
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