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[ CAS No. 42373-30-8 ] {[proInfo.proName]}

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Chemical Structure| 42373-30-8
Chemical Structure| 42373-30-8
Structure of 42373-30-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 42373-30-8 ]

CAS No. :42373-30-8 MDL No. :MFCD04038972
Formula : C6H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :GTPZHMGXKZIHKW-UHFFFAOYSA-N
M.W : 122.12 Pubchem ID :2761033
Synonyms :

Calculated chemistry of [ 42373-30-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.03
TPSA : 55.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.59
Log Po/w (XLOGP3) : 0.18
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.84
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.14
Solubility : 8.89 mg/ml ; 0.0728 mol/l
Class : Very soluble
Log S (Ali) : -0.91
Solubility : 14.9 mg/ml ; 0.122 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.57
Solubility : 3.3 mg/ml ; 0.027 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 42373-30-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42373-30-8 ]

* 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 [ 42373-30-8 ]
  • Downstream synthetic route of [ 42373-30-8 ]

[ 42373-30-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 86847-71-4 ]
  • [ 42373-30-8 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: Heating / reflux
Stage #2: With potassium carbonate In hexane
Example 25C
4-aminonicotinaldehyde
A solution of Example 25B (870 mg, 4.2 mmol) in 3N HCl (aq.) (10 mL) was heated to reflux overnight, and extracted three times with diethyl ether.
The aqueous layer was adjusted to pH>7 with solid K2CO3 and extracted six times with 20percent isopropanol/chloroform.
The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product (450 mg; 87percent).
40% for 8 h; Reflux N-(3-Formylpyridin-4-yl)pivalamide (245 mg, 1.20 mmol) was dissolved in 3 N HCI (2.47 mL) and heated to reflux for 8 h. TLC showed complete consumption of starting material. The mixture was ectracted with diethylether. The aqueous phase was made alkali with K2C03 and extracted with chloroform. The organic layer was dried over MgS04 and concentrated under reduced pressure. The crude was purified by column chromatography to give 4-aminonicotinaldehyde (57 mg, 40 percent).
40% for 8 h; Reflux Step 3:
N-(3-Formylpyridin-4-yl)pivalamide (245 mg, 1.20 mmol) was dissolved in 3 N HCl (2.47 mL) and heated to reflux for 8 h. TLC showed complete consumption of starting material.
The mixture was extracted with diethylether.
The aqueous phase was made alkali with K2CO3 and extracted with chloroform.
The organic layer was dried over MgSO4 and concentrated under reduced pressure.
The crude was purified by column chromatography to give 4-aminonicotinaldehyde (57 mg, 40percent).
Reference: [1] Patent: US2003/187026, 2003, A1,
[2] Patent: US2003/199511, 2003, A1, . Location in patent: Page/Page column 24
[3] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3401 - 3408
[4] Synthesis, 1999, # 6, p. 959 - 964
[5] Patent: WO2013/13817, 2013, A1, . Location in patent: Page/Page column 144
[6] Patent: US2013/29961, 2013, A1, . Location in patent: Paragraph 0817
  • 2
  • [ 266353-32-6 ]
  • [ 42373-30-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 77 - 82
  • 3
  • [ 138116-34-4 ]
  • [ 42373-30-8 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1202 - 1206
  • 4
  • [ 116026-93-8 ]
  • [ 42373-30-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 16, p. 3023 - 3025
  • 5
  • [ 1074-98-2 ]
  • [ 42373-30-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 77 - 82
  • 6
  • [ 123367-22-6 ]
  • [ 42373-30-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 77 - 82
  • 7
  • [ 504-24-5 ]
  • [ 42373-30-8 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3401 - 3408
[2] Patent: WO2013/13817, 2013, A1,
[3] Patent: US2013/29961, 2013, A1,
  • 8
  • [ 98400-69-2 ]
  • [ 42373-30-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 16, p. 3023 - 3025
  • 9
  • [ 70298-89-4 ]
  • [ 42373-30-8 ]
Reference: [1] Synthesis, 1999, # 6, p. 959 - 964
[2] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3401 - 3408
[3] Patent: WO2013/13817, 2013, A1,
[4] Patent: US2013/29961, 2013, A1,
  • 10
  • [ 42373-30-8 ]
  • [ 138116-34-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[2] Patent: WO2013/13817, 2013, A1, . Location in patent: Page/Page column 144
[3] Patent: US2013/29961, 2013, A1, . Location in patent: Paragraph 0818
  • 11
  • [ 113-24-6 ]
  • [ 42373-30-8 ]
  • [ 197507-59-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 16, p. 3023 - 3025
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