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[ CAS No. 1206979-33-0 ] {[proInfo.proName]}

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Chemical Structure| 1206979-33-0
Chemical Structure| 1206979-33-0
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Product Details of [ 1206979-33-0 ]

CAS No. :1206979-33-0 MDL No. :MFCD17010105
Formula : C6H4ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :AAJIQIWPVIWCGA-UHFFFAOYSA-N
M.W : 153.57 Pubchem ID :56932109
Synonyms :

Calculated chemistry of [ 1206979-33-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.9
TPSA : 41.57 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 2.24
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.662 mg/ml ; 0.00431 mol/l
Class : Soluble
Log S (Ali) : -1.92
Solubility : 1.85 mg/ml ; 0.0121 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.14
Solubility : 0.112 mg/ml ; 0.000728 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 1206979-33-0 ]

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 [ 1206979-33-0 ]

* 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 [ 1206979-33-0 ]
  • Downstream synthetic route of [ 1206979-33-0 ]

[ 1206979-33-0 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 871836-50-9 ]
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Reference: [1] Patent: EP1772454, 2007, A1, . Location in patent: Page/Page column 63
  • 2
  • [ 1060811-62-2 ]
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YieldReaction ConditionsOperation in experiment
53.4% With hydrazine hydrate In 1,2-dimethoxyethane at 75℃; for 16 h; To a stirred solution of 4,6-dichloronicotinaldehyde (3 x 1.0 g, 1.0 eq) in DME (3 x 14 mL), hydrazine hydrate (3 x 1.14 g, 4.0 eq, 99percent) was added slowly in a vial. The vial was sealed and the contents heated at 75°C for 16 h. After TLC showed completion, the mixture was cooled to rt and diluted with water (3 x 10 mL) and EtOAc (3 x 10 mL). After combining all 3 mixtures, the layers were separated and the organic layer was washed with brine (20 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The resulting crude was purified by flash chromatography (Combiflash® - Redisep, 12 g) using MeOH in DCM as eluent. The desired product was eluted at 1percent MeOH in DCM. The fractions with product were concentrated to obtain pure 6-chloro- lH-pyrazolo[4,3-c]pyridine as yellow solid (1.4 g, 53.43percent, from 3 batches). 1H NMR (400 MHz, DMSO-d6): δ 13.608 (s, 1H), 8.946 (s, 1H), 8.350 (s, 1H), 7.652 (s, 1H). LCMS calculated for (M) 423.15 and found (M+H) 424.23.
41% With N-ethyl-N,N-diisopropylamine; hydrazine In N,N-dimethyl acetamide at 80℃; for 4 h; Part III-- Synthesis of 6-chloro-1H-pyrazolo[4,3-c]pyridine [0232] 4,6-Dichloropyridine-3-carbaldehyde (3.7 g, 32 mmol), hydrazine (3.5 mL, 1 10 mmol) and N,N-diisopropylethylamine (20 mL) were combined in DMA (100 mL) and stirred at 80 °C for four hours. Then, the solution was cooled to room temperature, diluted with EtOAc, and washed three times with water and then with brine. The organic solution was concentrated and the resulting mixture was precipitated from dichloromethane to give 6- chloro-lH-pyrazolo[4,3-c]pyridine. Yield 2 g (41percent). LCMS (ESI): calc. C6H4C1N3 = 153; obs. M+H = 154.
38% With hydrazine In 1,4-dioxane; water at 150℃; for 18 h; Sealed tube To a reaction vessel containing a mixture of 4,6-dichloronicotinaldehyde (300 g, 1.7 mol) in 1,4- dioxane (1200 mL) was added hydrazine (50percent> in water)(360 mL, 3.6 mol). The reaction vessel was sealed and heated at 150 °C over 18 h. The mixture was cooled to room temperature, concentrated in vacuo, poured over water and filtered. The filter cake was washed with 20percent> EtOAc in hexanes and dried to afford 6-chloro-lH-pyrazolo[4,3-c]pyridine (101.4 g, 38 percent>) as a light-yellow solid. LCMS (ESI) [M+H]+ = 154.
Reference: [1] Patent: WO2015/38417, 2015, A1, . Location in patent: Page/Page column 78
[2] Patent: WO2013/169704, 2013, A2, . Location in patent: Paragraph 0232
[3] Patent: WO2014/210354, 2014, A1, . Location in patent: Page/Page column 41
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5648 - 5652
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  • [ 871836-50-9 ]
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Reference: [1] Patent: EP1772454, 2007, A1, . Location in patent: Page/Page column 63
  • 4
  • [ 73998-95-5 ]
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Reference: [1] Patent: WO2013/169704, 2013, A2,
[2] Patent: WO2015/38417, 2015, A1,
  • 5
  • [ 65973-52-6 ]
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Reference: [1] Patent: WO2013/169704, 2013, A2,
[2] Patent: WO2014/210354, 2014, A1,
  • 6
  • [ 6975-44-6 ]
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Reference: [1] Patent: WO2015/38417, 2015, A1,
[2] Patent: WO2015/38417, 2015, A1,
  • 7
  • [ 105-50-0 ]
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Reference: [1] Patent: WO2015/38417, 2015, A1,
[2] Patent: WO2015/38417, 2015, A1,
  • 8
  • [ 40296-46-6 ]
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Reference: [1] Patent: WO2015/38417, 2015, A1,
[2] Patent: WO2015/38417, 2015, A1,
  • 9
  • [ 1830-54-2 ]
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Reference: [1] Patent: WO2014/210354, 2014, A1,
  • 10
  • [ 79398-27-9 ]
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Reference: [1] Patent: WO2014/210354, 2014, A1,
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