Home Cart 0 Sign in  
X

[ CAS No. 20348-23-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 20348-23-6
Chemical Structure| 20348-23-6
Chemical Structure| 20348-23-6
Structure of 20348-23-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 20348-23-6 ]

Related Doc. of [ 20348-23-6 ]

Alternatived Products of [ 20348-23-6 ]

Product Details of [ 20348-23-6 ]

CAS No. :20348-23-6 MDL No. :MFCD09025907
Formula : C7H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :QQVXDMFULJVZLA-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :13196538
Synonyms :

Calculated chemistry of [ 20348-23-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.86
TPSA : 34.15 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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 0.31
Log Po/w (MLOGP) : 0.28
Log Po/w (SILICOS-IT) : 1.43
Consensus Log Po/w : 0.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.71 mg/ml ; 0.0199 mol/l
Class : Very soluble
Log S (Ali) : -1.21
Solubility : 8.34 mg/ml ; 0.0613 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.627 mg/ml ; 0.0046 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 20348-23-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20348-23-6 ]

* 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 [ 20348-23-6 ]
  • Downstream synthetic route of [ 20348-23-6 ]

[ 20348-23-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 20348-23-6 ]
  • [ 34950-82-8 ]
YieldReaction ConditionsOperation in experiment
69.5% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 2 h; To a solution of 3, 4-dihydro-2H-pyrido [3, 2-b] [1, 4] oxazine (500 mg, 3.67 mmol) in DMF (10 mL) was added NBS (719 mg, 4.04 mmol) at 0°C. The mixture was stirred at 0°C for 2 h. The mixture was quenched with sat. NaHCO3 aq. ' and water at 0°C and stirred at 0°C for 20 min. The precipitate was collected by filtration. The solid was washed with water and dried in vacuo to give the title compound (549 mg, 2.55 mmol, 69.5percent) as brown solids. . . (3284) MS (ESI+), found 215.2 (M+H) (3285) 1H NMR (300 MHz, CDC13) 5:3.50-3.58 (2H, m) , 4.18-4.26 (2H, m) , 4.82 (1H, brs), 7.10 (1H, d, J = 1.9 Hz), 7.72 (1H, d, J = 2.3 Hz)
28% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1 h; (Example 5 Synthesis of Compounds I-114, I-110, and I-111) [Show Image][Show Image]Step 1 To a solution of Compound (14) (4.00 g, 29.4 mmol) in dimethylformamide (40 mL), N-bromosuccinimide (6.27 g, 35.3 mmol) was added. The solution was then stirred at room temperature for 1 hour. Aqueous saturated sodium bicarbonate (100 mL) and water (100 mL) were then thereto. The precipitated powder was filtered, and then washed with water. The filtrate was then extracted with diisopropyl ether. The organic layer was washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield subject compound (15) (1.79 g, 28percent) as a pale yellow powder.1H-NMR (DMSO-d6) δ7.62 (1H, d, J= 2.1Hz), 7.14 (1H, d, J =2.1Hz), 6.98 (1H, br s), 4.11 (2H, t, J=4.5Hz), 3.36-3.40 (2H, m) LC/MS (Method A): 0.98 min, [M+H]+= 217.0.
Reference: [1] Patent: WO2018/30550, 2018, A1, . Location in patent: Paragraph 0596
[2] Patent: EP2341052, 2011, A1, . Location in patent: Page/Page column 40
[3] Acta Chemica Scandinavica (1947-1973), 1971, vol. 25, p. 3135 - 3143
[4] Patent: KR101576386, 2015, B1, . Location in patent: Paragraph 0158-0160
  • 2
  • [ 20348-09-8 ]
  • [ 20348-23-6 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 18 h; Heating / reflux
Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃;
a) 3,4-Dihydro-2H-pyrido[3,2-][l,4]oxazine; To an ice-cold solution of 4H-ρyrido[3,2-][l,4]oxazin-3-one (5.00 g, 33.3 mmol) in TηF (40 mL) was added lithium aluminum hydride (66.6 mL of a 1.0 M solution in TηF, 66.6 mmol). Following the addition, the solution was heated to reflux. After 18 h, the solution was cooled to 00C and quenched the reaction with H&2O (4 mL) followed by NaOH (4 mL, 15percent) and H2O (10 mL). The resulting slurry was filtered over Celite and the filtrate concentrated to give the title compound (3.87 g, 85percent) as a blue-gray powder: 1H NMR (500 MHz, OMSO-d6) δ 7.53 (dd, J= 4.5, 1.0 Hz, IH), 6.90-6.89 (m, IH), 6.61 (br s, IH), 6.44 (dd, J= 8.0, 3.0 Hz, IH), 4.08 (t, J= 4.5 Hz, 2H), 3.39-3.36 (m, 2H); MS (ESI) m/e \\31 (M + η)\\
79% With sodium hydroxide; LiAlH4 In tetrahydrofuran a)
3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine
To a suspension of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g, 13.3 mmole) in dry THF (40 mL) was added a solution of LiAlH4 in THF (1.0 M, 26.6 mL, 26.6 mmole) slowly at 0°C.
After 1 hr the mixture was quenched with 2.0 M NaOH until a solid formed.
The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.44 g, 79percent) as a white solid which was sufficiently pure for use in the next step: MS (ES) m/e 137 (M + H)+.
Reference: [1] Patent: WO2007/53131, 2007, A2, . Location in patent: Page/Page column 133
[2] Patent: EP1226138, 2004, B1,
[3] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324
[4] Patent: US2008/305169, 2008, A1,
[5] Patent: US2007/10670, 2007, A1, . Location in patent: Page/Page column 92
[6] Patent: US2008/64871, 2008, A1, . Location in patent: Page/Page column 56
  • 3
  • [ 34950-82-8 ]
  • [ 20348-23-6 ]
YieldReaction ConditionsOperation in experiment
17% With potassium carbonate; tricyclohexylphosphine In water; toluene at 115℃; for 96 h; Inert atmosphere; Sealed tube In an open sealed tube, a stirred mixture of 7-bromo-3,4-dihydro-2-pyrido[3,2- b][l,4]oxazoline (Maybridge, United Kingdom) (108 mg, 0.5 mmol), palladium(II) acetate (11 mg, 0.05 mmol), tricyclohexylphosphine (28 mg, 0.1 mmol), K2C03 (276 mg, 2.0 mmol) and ira/i5,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (159 mg, 0.6 mmol) in toluene (3 mL) and H20 (1 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, heated to 115 °C and stirred for 4 days. After allowing to cool, the reaction mixture was filtered through Celite and the filter cake washed with EtOAc (3 x 20 mL), H20 (10 mL) and EtOAc (20 mL). The aqueous and organic layers of the filtrate were partitioned and the aqueous layer extracted with EtOAc (1 x 20 mL). The combined organic extracts were dried (Na2S04), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (4 prep TLC plates used) using EtOAc as eluent to give the product (21 mg, 17percent) as a solid.[00232] 1H NMR (CDC13, 300MHz): δ 7.54 (s, 1H), 6.70 (d, / = 1.6 Hz, 1H), 4.99 (br. s, 1H), 4.21 (dt, / = 4.4, 0.7 Hz, 2H), 3.53 (t, / = 4.4 Hz, 2H), 2.26-2.19 (m, 1H), 1.74-1.61 (m, 1H), 1.33-1.26 (m, 1H), 1.10-1.03 (m, 1H). 13C NMR (CDC13, 75MHz): δ 146.6, 139.8, 138.8, 128.0 (q, / = 269 Hz), 125.4, 120.7, 65.0, 40.8, 22.7 (q, / = 36.7 Hz), 17.0 (q, / = 2.8 Hz), 10.2 (q, J = 2.2 Hz). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = 245.09 (M+H)+ HRMS (EI): [M+H]+ calc'd for C11H11F3N2O m/z 245.0902, found 245.0909.[00233] Also obtained from the preparative thin-layer chromatography plates was recovered 7-bromo-3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (18 mg, 17percent) and reduced starting material, 3,4-dihydro-2-pyrido[3,2-b][l,4]oxazoline (9.4 mg, 14percent). Note: the above reaction also was successfully undertaken using the alternative ligands 2- dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, or 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl.
Reference: [1] Patent: WO2012/75316, 2012, A2, . Location in patent: Page/Page column 55
  • 4
  • [ 149-73-5 ]
  • [ 20348-23-6 ]
Reference: [1] Patent: US2015/119385, 2015, A1, . Location in patent: Paragraph 0692; 0693
[2] Patent: WO2015/59668, 2015, A1, . Location in patent: Page/Page column 106
  • 5
  • [ 16867-03-1 ]
  • [ 20348-23-6 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324
  • 6
  • [ 959992-62-2 ]
  • [ 20348-23-6 ]
Reference: [1] Patent: US2015/119385, 2015, A1,
  • 7
  • [ 959992-62-2 ]
  • [ 20348-23-6 ]
Reference: [1] Patent: WO2015/59668, 2015, A1,
Recommend Products
Same Skeleton Products
Historical Records

Related Parent Nucleus of
[ 20348-23-6 ]

Other Aromatic Heterocycles

Chemical Structure| 20348-09-8

[ 20348-09-8 ]

2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.86

Chemical Structure| 34950-82-8

[ 34950-82-8 ]

7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Similarity: 0.85

Chemical Structure| 351447-07-9

[ 351447-07-9 ]

6-Iodo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Similarity: 0.84

Chemical Structure| 959992-62-2

[ 959992-62-2 ]

6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Similarity: 0.84

Chemical Structure| 122450-96-8

[ 122450-96-8 ]

7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.75