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[ CAS No. 20348-21-4 ] {[proInfo.proName]}

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Chemical Structure| 20348-21-4
Chemical Structure| 20348-21-4
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Product Details of [ 20348-21-4 ]

CAS No. :20348-21-4 MDL No. :MFCD10000810
Formula : C9H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DMLNXUUGRSBBBR-UHFFFAOYSA-N
M.W : 178.19 Pubchem ID :88501
Synonyms :

Calculated chemistry of [ 20348-21-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.71
TPSA : 51.22 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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 0.73
Log Po/w (WLOGP) : 0.62
Log Po/w (MLOGP) : 0.4
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 0.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 3.2 mg/ml ; 0.0179 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 7.35 mg/ml ; 0.0413 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.171 mg/ml ; 0.000959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.3

Safety of [ 20348-21-4 ]

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

Application In Synthesis of [ 20348-21-4 ]

* 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 [ 20348-21-4 ]
  • Downstream synthetic route of [ 20348-21-4 ]

[ 20348-21-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 16867-03-1 ]
  • [ 600-00-0 ]
  • [ 20348-21-4 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In acetone at 70℃; for 16 h; Step-(i): Synthesis of 2,2-dimethyl-2H-pyridor3,2-biri,41oxazin-3(4H)-one (18.1) To a stirred solution of 2-aminopyridin-3-ol (5 g, 45.45 mmol) in acetone (50 mL) was added K2CO3 (25.09 g, 181.81 mmol) followed by ethyl 2-bromo-2-methylpropanoate (13.29 g, 68.18 mmol) at 20-35°C and the reaction mixture was allowed to stir at 70°C for 16 h. Then the reaction mixture was cooled to 20-35°C and diluted with ice water. The obtained solid was filtered and washed with water to get the desired compound as a white solid (5 g, 97percent); H NMR (400MHz, DMSO-<) δ 11.17 (s, 1H), 7.91 (d, /=4.4 Hz, 1H), 7.34 (d, /=7.8 Hz, 1H), 6.98 (dd, /=4.9 Hz, 7.9 Hz, 1H), 1.41 (s, 6H); LC-MS: 179.3 (M+l)+.
Reference: [1] Patent: WO2015/71780, 2015, A1, . Location in patent: Page/Page column 22
[2] Tetrahedron Letters, 2010, vol. 51, # 14, p. 1852 - 1855
[3] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324
  • 2
  • [ 16867-03-1 ]
  • [ 20348-21-4 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 262 - 267
  • 3
  • [ 20348-21-4 ]
  • [ 894852-01-8 ]
YieldReaction ConditionsOperation in experiment
86% With bromine; sodium carbonate In dichloromethane at 0 - 35℃; for 16 h; Step-(ii): Synthesis of 7-bromo-2.2-dimethyl-2H-pyridor3.2-biri.41oxazin-3(4H)-one (Intermediate- 18) To a stirred solution of 2,2-dimethyl-2H-pyrido[3,2-b][l ,4]oxazin-3(4H)-one (18.1) (2 g, 11.23 mmol) in DCM (20 mL) was added Na2C03 (3.57 g, 33.70 mmol) followed by bromine (0.92 mL, 17.97 mmol) at 0°C and the reaction mixture was allowed to stir at 20- 35°C for 16 h. Then the reaction mixture was diluted with ice water, obtained solid was filtered and washed with water to get the desired compound as a white solid (1.8 g, 86percent); lU NMR (400MHz, DMSO-<) δ 11.39 (s, 1H), 8.04 (d, J=\.9 Hz, 1H), 7.66 (d, /=1.4 Hz, 1H), 1.43 (s, 6H); LC-MS: 257.0 (M+l)+.
Reference: [1] Patent: WO2015/71780, 2015, A1, . Location in patent: Page/Page column 22
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