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Product Details of [ 20348-09-8 ]

CAS No. :20348-09-8 MDL No. :MFCD00006697
Formula : C7H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ANHQLUBMNSSPBV-UHFFFAOYSA-N
M.W : 150.14 Pubchem ID :88499
Synonyms :

Calculated chemistry of [ 20348-09-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.06
TPSA : 51.22 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) : -7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : -0.16
Log Po/w (MLOGP) : -0.26
Log Po/w (SILICOS-IT) : 1.06
Consensus Log Po/w : 0.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.26
Solubility : 8.2 mg/ml ; 0.0546 mol/l
Class : Very soluble
Log S (Ali) : -0.77
Solubility : 25.4 mg/ml ; 0.169 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.868 mg/ml ; 0.00578 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 20348-09-8 ]

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 [ 20348-09-8 ]

* 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 [ 20348-09-8 ]
  • Downstream synthetic route of [ 20348-09-8 ]

[ 20348-09-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 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
  • 2
  • [ 16867-03-1 ]
  • [ 79-04-9 ]
  • [ 20348-09-8 ]
YieldReaction ConditionsOperation in experiment
4.3 g With sodium hydrogencarbonate In water; butanone at 20 - 75℃; for 1.5 h; Cooling with ice 2-Amino-3-ol (45 mmol) and sodium hydrogen carbonate (51 mmol) in water (30 ml) and 2-butanone (30 ml) mixed solution. Under ice-cooling, chloroacetyl chloride (51 mmol) of 2-butanone (10 ml) was slowly added, maintaining the temperature during the addition does not exceed 10 ° C. It was stirred at room temperature for 30 minutes, stirring for 1 hour at 75 ° C, and concentrated recrystallization (methanol / water = 1: 1) to give 4.3 g of the title compound.
Reference: [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Helvetica Chimica Acta, 1976, vol. 59, p. 1593 - 1612
[3] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0605-0607
  • 3
  • [ 1268818-15-0 ]
  • [ 20348-09-8 ]
YieldReaction ConditionsOperation in experiment
77% for 2.5 h; Inert atmosphere; Reflux General procedure: To a stirred solution of 2a (2 mmol) in acetic acid (10 mL), powdered Fe (12 mmol) was added and the reaction mixture was then refluxed for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and the acetic acid was removed under reduced pressure, EtOAc (20 mL) was added and was stirred for 2 min and then filtered to remove any iron impurities. The insoluble iron residue was washed with EtOAc (20 mL). The filtrate and washings were combined and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude product thus obtained was purified by column chromatography to obtain the pure product 3a.
Reference: [1] Tetrahedron, 2011, vol. 67, # 6, p. 1187 - 1192
  • 4
  • [ 16867-03-1 ]
  • [ 5292-43-3 ]
  • [ 20348-09-8 ]
YieldReaction ConditionsOperation in experiment
2.3 g With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; A mixture of 3-hydroxy-2-aminopyridine 2 (3 g, 27 mmol), tert-butylbromoacetate3 (4 mL, 27 mmol), Adogen-464 (168 mg) and NaOH solution (40percent in water, 15 mL) was dissolved in DCM (25 mL).The reaction mixture was stirred at room temperature for 24 h. Themixture was then washed with water (3 × 50 mL) and the organic layerscombined. The organic portion was dried, (MgSO4) and concentratedin vacuo. The resulting crude yellow oil was purified by columnchromatography (silica gel, 3percent MeOH in DCM) to afford amine 4:Yellow oil; yield 2.3 g, 38percent; Rf (5percent MeOH in DCM) 0.50; IR (νmax,cm–1) film: 3483 (w), 1748 (s), 1616 (s), 1476 (s), 1154 (s); 1H NMR(300 MHz, CDCl3) δ 7.67 (1H, d, J = 5 Hz, H py), 6.80 (1H, d, J = 8 Hz,H py), 6.55 (1H, dd, J = 8, 5 Hz, H py), 4.85 (2H, br. s, NH2), 4.49 (2H,s, CH2), 1.45 (9H, s, 3 × CH3); 13C NMR (75 MHz, CDCl3) δ 167.7 (s),150.7 (s), 140.9 (s), 140.1 (d), 117.7 (d), 113.3 (d), 82.9 (s), 66.3 (t), 28.2(q); LRMS (ES) m/z (percent): 266 [M + H + CH3CN]+ (30).3–5
Reference: [1] Journal of Chemical Research, 2016, vol. 40, # 12, p. 753 - 757
  • 5
  • [ 16867-03-1 ]
  • [ 79-11-8 ]
  • [ 20348-09-8 ]
Reference: [1] Patent: WO2004/14384, 2004, A2, . Location in patent: Page/Page column 256; 262
  • 6
  • [ 16867-03-1 ]
  • [ 105-36-2 ]
  • [ 20348-09-8 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 14, p. 1852 - 1855
  • 7
  • [ 337463-88-4 ]
  • [ 201230-82-2 ]
  • [ 20348-09-8 ]
  • [ 443956-11-4 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 24, p. 3315 - 3321
  • 8
  • [ 16867-03-1 ]
  • [ 20348-09-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1081 - 1086
[2] Patent: US2016/145268, 2016, A1,
  • 9
  • [ 15128-82-2 ]
  • [ 20348-09-8 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 6, p. 1187 - 1192
  • 10
  • [ 93765-25-4 ]
  • [ 20348-09-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1081 - 1086
  • 11
  • [ 93765-23-2 ]
  • [ 20348-09-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1081 - 1086
  • 12
  • [ 93765-24-3 ]
  • [ 20348-09-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1081 - 1086
  • 13
  • [ 16867-03-1 ]
  • [ 96-34-4 ]
  • [ 20348-09-8 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1969, vol. 23, p. 2322 - 2324
  • 14
  • [ 20348-09-8 ]
  • [ 122450-96-8 ]
YieldReaction ConditionsOperation in experiment
76% With bromine In N,N-dimethyl-formamide at 20℃; To a solution of compound 15 (1 g, 6.66 mmol) in DMF (30 mL) was added dropwise bromine (0.480 mL, 9.32 mmol). The reaction mixture was stirred overnight at room temperature. Water was added and a precipitate was formed which was collected by filtration and dried in lyophilizer overnight to afford title compound 16 (1.16 g, 76percent yield). IH NMR <n="95"/>(DMSO-d6) δ (ppm): 11.43 (s, IH), 8.04 (d, J = 2.0 Hz, IH), 7.65 (d, J = 2.0 Hz, IH), 4.67 (s,2H).
69% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 72 h; a) 7-Bromo-2H-pyrido[3,2-jb][1 ,4]oxazin-3(4H)-oneA mixture of 2H-pyrido[3,2-d][1 ,4]oxazin-3(4H)-one (1.30 g, 8.66 mmol) and N-bromosuccinimide (1.70 g, 9.53 mmol) in DMF (30 mL) was stirred for three days at room temperature . Water (10 mL) was added and the suspension was cooled EPO <DP n="58"/>with an ice bath. The resulting precipitate was filtered, washed with water, and air- dried in a Buchner funnel to give the title compound (1.37 g, 69percent) as a white solid.MS(ES+) m/e 229 [M+H]+.
260 mg With bromine In N,N-dimethyl-formamide at 20℃; for 2 h; the step A compound (3.24mmol) was dissolved in 14 ml of N, N- dimethylformamide, then slowly added Bromine(3.56 mmol). At room temperature it wasstirred for 2 hours then water (300 ml) wasadded .the resulting precipitate was collected by filtration then it was washed with water and dried to give 260 mg ofthe title compound.
Reference: [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 2, p. 133 - 142
[2] Patent: WO2009/100536, 2009, A1, . Location in patent: Page/Page column 93-94
[3] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 56-57
[4] Patent: US4906629, 1990, A,
[5] Patent: US4822794, 1989, A,
[6] Patent: US4866074, 1989, A,
[7] Patent: WO2004/14384, 2004, A2, . Location in patent: Page/Page column 256; 262
[8] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0608-0610
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