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[ CAS No. 73896-36-3 ] {[proInfo.proName]}

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Chemical Structure| 73896-36-3
Chemical Structure| 73896-36-3
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Product Details of [ 73896-36-3 ]

CAS No. :73896-36-3 MDL No. :MFCD03206481
Formula : C6H7N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RDJILYVRVOTMTQ-UHFFFAOYSA-N
M.W : 169.14 Pubchem ID :3852428
Synonyms :

Calculated chemistry of [ 73896-36-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.96
TPSA : 93.96 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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.71
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 0.59
Log Po/w (MLOGP) : -0.7
Log Po/w (SILICOS-IT) : -1.49
Consensus Log Po/w : 0.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.88
Solubility : 2.25 mg/ml ; 0.0133 mol/l
Class : Very soluble
Log S (Ali) : -2.76
Solubility : 0.294 mg/ml ; 0.00174 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.17
Solubility : 11.5 mg/ml ; 0.0678 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 73896-36-3 ]

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

Application In Synthesis of [ 73896-36-3 ]

* 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 [ 73896-36-3 ]
  • Downstream synthetic route of [ 73896-36-3 ]

[ 73896-36-3 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 38533-61-8 ]
  • [ 73896-36-3 ]
YieldReaction ConditionsOperation in experiment
74% With ammonia In methanol at 65℃; for 18 h; Example 26; 6- [({2- [6-(methyloxy)-3-oxopyrido [2,3-b] pyrazin-4(3H)-yl] -5,6,7,8- tetrahydro-6-quinazolinyl}amino)methyl]-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-one hydrochloride; (a) 6-(Methyloxy)-3 -nitro-2-pyridinamine; A solution/suspension of 2-chloro-6-(methyloxy)-3-nitropyridine (65.7 g, 348 mmol) in 2M ammonia in methanol (500 ml, 1000 mmol) and aqueous ammonia (500 ml, 348 mmol) was stirred at 65°C for 18h. The reaction was cooled down and the solid filtered off and washed with water (2x100ml). The solid was dried in the vacuum oven at 4O0C overnight to afford the product as a bright yellow solid (52.14g, 84percent purity by NMR, 74percent). MS (ES+) m/z 170 (MH+).
74% With ammonia In methanol at 65℃; for 18 h; Example 13A; (lR)-l-({4-[([l,3]Oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-l- piperidinyl}methyl)-l,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione hydrochloride; <n="57"/>(a) 6-(Methyloxy)-3 -nitro-2-pyridinamine; A solution/suspension of 2-chloro-6-(methyloxy)-3-nitropyridine (65.7 g, 348 mmol) in 2M ammonia in methanol (500 ml, 1000 mmol) and aqueous ammonia (500 ml, 348 mmol) was stirred at 65 0C for 18h. The reaction was cooled down and the solid filtered off and washed with water (2x100ml). The solid was dried in the vacuum oven at 4O0C overnight to afford the product as a bright yellow solid (52.14g, 84percent purity by NMR, 74percent).MS (ES+) m/z 170 (MH+).
74% With ammonia In DMF (N,N-dimethyl-formamide); water at 70℃; for 4.25 h; Preparation Example 1; '6-Methoxy-3-nitro-2-pyridineamine [Formula 50]; A solution of 2-chloro-6-methoxy-3- nitropyridine (25.3 g, 0.134 mol) and a concentrated aqueous ammonia solution (70 ml) in N,N- dimethylformamide (200 ml) was stirred at 70°C for 4 hours and 15 minutes. The reaction mixture was cooled to room temperature and then diluted with water. The resulted precipitate was collected by filtration to yield the title compound (16.8 g, 99.2 mmol, 74.0percent) as a yellow solid. 1H NMR(400 MHz, DMSO-d6) No.ppm; 3.90(3H, s), 6.16(lH, d, J=9Hz), 8.16 (2H, br s), 8.26(lH, d, J=9Hz).
86% With pyridine; ammonium carbonate In dichloromethane A.
6-Methoxy-3-nitro-pyridin-2-ylamine.
Scheme 8.
To a glass pressure vessel was added 2-chloro-6-methoxy-3-nitro-pyridine (10.0 g, 53 mmol), ammonium carbonate (12.4 g, 159 mmol) and pyridine (100 mL).
The mixture was heated at 40° C. for 24 h.
The reaction mixture was concentrated in vacuo, and the residue was taken up in CH2Cl2 and chromatographed (silica gel; CH2Cl2) yielding 7.6 g (86percent) of 6-methoxy-3-nitro-pyridin-2-ylamine.
HPLC: Rt=7.89. 1H NMR (400 MHz, DMSO-d6): 8.26 (d, J=9.1 Hz, 1H), 8.17 (br s, 2H), 6.15 (d, J=9.1 Hz, 1H), 3.89 (s, 3H).

Reference: [1] Patent: WO2008/128961, 2008, A1, . Location in patent: Page/Page column 24; 85
[2] Patent: WO2008/128942, 2008, A1, . Location in patent: Page/Page column 55-56
[3] Patent: WO2005/103049, 2005, A1, . Location in patent: Page/Page column 102-103
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1924 - 1928
[5] Patent: US2003/176438, 2003, A1,
[6] Patent: US2008/125358, 2008, A1, . Location in patent: Page/Page column 18
[7] Patent: WO2009/87153, 2009, A1, . Location in patent: Page/Page column 47-48
[8] Patent: US2009/306089, 2009, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 124-41-4 ]
  • [ 27048-04-0 ]
  • [ 73896-36-3 ]
YieldReaction ConditionsOperation in experiment
86.5% at 15 - 30℃; for 4 - 5 h; Sodium methoxide, 7.78 gm (0.144 mole) and methanol 50.0 ml were mixed and cooled to 15° C.
To this solution, 25.0 gm of 2-amino-6-chloro-3-nitropyridine (0.144 mole) was added while maintaining the temperature at 15° C. by external cooling.
The resulting mixture was heated to 25°-30° C. and maintained at this temperature for 4-5 hrs with constant stirring.
The completion of reaction was monitored by TLC.
After the completion of reaction, the reaction mixture was poured in water.
The precipitate thus obtained was filtered and washed with water.
On drying 21.0 gm of 2-amino-3-nitro-6-methoxypyridine (86.5percent yield) was obtained, with the HPLC purity of 99.0percent.
Melting point 167°-169° C.; 1H-NMR (CDCl3) δ 3.89 ppm (s,-3H, OCH3), 66.14-6.16 ppm (d, 1H), 68.24-8.27 ppm (d, 1H), 68.16 ppm (s, -2H, -NH2).
84.1% at 20℃; for 3 h; To a solution of 2-amino-3-nitro-6-chloropyridine (300 mg, 1.73 mmol, an intermediate in preparation of 8) in 5 mL anhydrous DMF was added sodium methoxide (187mg, 3.46 mmol). This mixture was stirred at room temperature for 3 h then poured onto 20 g crushed ice and extracted with ethyl acetate. The extracts were dried, evaporated and purified by column chromatography on silica gel (PE/AcOEt=5:1) to give 2-amino-3-nitro-6-methoxylpyridine (246 mg, 84.1percent) as yellow solid. Next steps followed the general procedure, and the title compound was obtained as white solid (188 mg, 67.0percent over 2 steps). IR (KBr) ν 3246, 3184, 1708, 1635, 1599, 1488, 1462, 1341, 1260, 1024, 839cm−1; 1H NMR (400MHz, DMSO-d6) δ 3.81 (3H, s, CH3), 6.56 (1H, d, J=8.4Hz, H-7), 7.42 (1H, d, J=8.4Hz, H-8), 11.82 (1H, s, NH-1), 12.25 (1H, s, NH-4); 13C NMR (100MHz, DMSO-d6) δ 53.50, 104.56, 115.19, 126.61, 136.21, 154.35, 156.11, 158.55; HRMS-EI C8H7N3O3 calcd [M+Na]+ 216.0385, found 216.0382.
9 g at -15 - 20℃; for 16 h; To a stirred solution of Compound 39b (15g,86.70mmol) in MeOH (35ml) was added NaOMe (7.2g,133.92mmol) at -15°C and stirred for 16h at RT. The reaction was quenched with ice and the obtained solids were filtered and dried to afford the required compound (9g).
Reference: [1] Patent: US2006/80790, 2006, A1, . Location in patent: Page/Page column 3
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 19 - 32
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1808 - 1819
[4] Patent: WO2014/57415, 2014, A2, . Location in patent: Page/Page column 47
  • 3
  • [ 67-62-9 ]
  • [ 5446-92-4 ]
  • [ 7646-85-7 ]
  • [ 73896-36-3 ]
YieldReaction ConditionsOperation in experiment
87% With ammonium chloride; potassium <i>tert</i>-butylate In dimethyl sulfoxide Example 1
6-Methoxy-3-nitropyridine (154 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMSO (2 ml), and a resulting solution was added dropwise to a DMSO solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25° C.
After completion of the addition, the resulting mixture was stirred at 25 ° C. for 9 hours and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml).
A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1] to obtain 147 mg of 2-amino-6-methoxy-3-nitropyridine (yield: 87percent).
Reference: [1] Patent: US5648496, 1997, A,
  • 4
  • [ 5446-92-4 ]
  • [ 73896-36-3 ]
Reference: [1] Chemical Communications, 1998, # 15, p. 1519 - 1520
[2] Liebigs Annalen der Chemie, 1991, # 9, p. 875 - 878
[3] Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4878 - 4888
  • 5
  • [ 27048-04-0 ]
  • [ 73896-36-3 ]
Reference: [1] Patent: WO2004/92166, 2004, A2, . Location in patent: Page 71
[2] Patent: US5599812, 1997, A,
[3] Asian Journal of Chemistry, 2013, vol. 25, # 14, p. 7959 - 7966
  • 6
  • [ 17920-35-3 ]
  • [ 73896-36-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 7
  • [ 67-56-1 ]
  • [ 27048-04-0 ]
  • [ 73896-36-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 6, p. 1331 - 1338
  • 8
  • [ 45644-21-1 ]
  • [ 73896-36-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 9
  • [ 4684-94-0 ]
  • [ 73896-36-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 10
  • [ 159603-71-1 ]
  • [ 73896-36-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 11
  • [ 16013-85-7 ]
  • [ 73896-36-3 ]
Reference: [1] Patent: WO2014/57415, 2014, A2,
  • 12
  • [ 2402-78-0 ]
  • [ 73896-36-3 ]
Reference: [1] Patent: WO2014/57415, 2014, A2,
  • 13
  • [ 73896-36-3 ]
  • [ 27048-04-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1924 - 1928
  • 14
  • [ 1643-19-2 ]
  • [ 73896-36-3 ]
  • [ 84487-04-7 ]
YieldReaction ConditionsOperation in experiment
64% With phosphorus pentaoxide; hydrogen bromide; acetic acid In toluene B.
6-Bromo-3-nitro-pyridin-2-ylamine.
To a glass pressure vessel containing 6-methoxy-3-nitro-pyridin-2-ylamine (5.0 g, 29.5 mmol) was added 30percent hydrogen bromide/acetic acid (60 mL).
The vessel was sealed, and the contents were heated to 60° C. for 24 h.
The reaction mixture was cooled, and the solvent was removed in vacuo giving 6.8 g (>95percent) of crude 6-amino-5-nitro-pyridin-2-ol hydrobromide (HPLC: Rt=5.46).
This material (2.0 g, 8.5 mmol) was taken up in toluene (30 mL), followed by phosphorus pentoxide (2.4 g, 17.0 mmol) and tetrabutyl ammonium bromide (3.2 g, 9.7 mmol).
The mixture was heated to reflux for 4 h.
The reaction mixture was cooled to 0° C., diluted with saturated NaHCO3, and extracted with ethyl acetate (3*100 mL).
The combined organics were washed with water (100 mL) and dried (Na2SO4) to afford 1.18 g (64percent) of 6-bromo-3-nitro-pyridin-2-ylamine.
HPLC: Rt=8.17. 1H NMR (400 MHz, DMSO-d6): 8.33 (br s, 2H), 8.32 (d, J=8.6 Hz, 1H), 6.96 (d, J=8.6 Hz, 1H).
Reference: [1] Patent: US2003/176438, 2003, A1,
  • 15
  • [ 73896-36-3 ]
  • [ 113713-60-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 10080 - 10100
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1371 - 1375
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304
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