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[ CAS No. 69879-22-7 ] {[proInfo.proName]}

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Chemical Structure| 69879-22-7
Chemical Structure| 69879-22-7
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Product Details of [ 69879-22-7 ]

CAS No. :69879-22-7 MDL No. :MFCD09757481
Formula : C6H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :BMNPVMQSUPTGFD-UHFFFAOYSA-N
M.W : 122.12 Pubchem ID :18404634
Synonyms :

Calculated chemistry of [ 69879-22-7 ]

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) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : -0.03
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.43
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 0.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.01
Solubility : 12.1 mg/ml ; 0.0987 mol/l
Class : Very soluble
Log S (Ali) : -0.7
Solubility : 24.6 mg/ml ; 0.202 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 : 1.21

Safety of [ 69879-22-7 ]

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

Application In Synthesis of [ 69879-22-7 ]

* 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 [ 69879-22-7 ]
  • Downstream synthetic route of [ 69879-22-7 ]

[ 69879-22-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4214-73-7 ]
  • [ 69879-22-7 ]
YieldReaction ConditionsOperation in experiment
73.16% With lithium aluminium tetrahydride In tetrahydrofuran for 1.5 h; To a solution of compound 53.9 (10 g, 83.95 mmol, 1 eq) in THF (150 mL) wasadded LAH (6.37 g, 167.90 mmol, 2 eq) at 0°C. The mixture was stirred at 0°C for 1.5 hours.The reaction mixture was quenched by addition saturated sodium sulfate at 0 °C and added100 ml H20 then extracted with ethyl acetate (100 mL x 3). The combined organic layerswere washed with saturated brines (30 mL x 1), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure to give the product compound 53.8 (7.50 g, 61.42mmol, 73.16percent yield) as a yellow oil. LCMS (ESI): m/z: [M + H] called for C6H6N20: 123;found 123; RT=0.099 mm.
30% With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; 4.1.1
Synthesis of 6-aminopyridine-3-carboxaldehyde
A 1M solution of diisobutylaluminum hydride (DIBAL) in hexane (10 mL) was added to a solution of 6-amino-5-cyanopyridine (10 mmol) in dry THF (50 mL) cooled at 0 °C.
The ice-bath was removed, and additional 7.1 mL of a 1M solution of DIBAL in hexane were added in two successive portions.
After stirring for additional 30 min, the reaction was quenched by the dropwise addition of dry MeOH (15 mL).
The mixture was partitioned between 100 mL of AcOEt and 70 mL of 2N HCl.
The aqueous layer was treated with 75 mL of 2N NaOH and extracted with AcOEt.
The organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to dryness.
The residue was purified by column chromatography on silica gel eluting with CHCl3/AcOEt 1:4. Yield: 30percent, mp = 174-175 °C. IR (KBr): 3366, 3121, 1659 cm-1. 1H NMR (CD3OD, 400 MHz): δ (ppm) 9.67 (s, 1H, CHO), 8.41 (d, 1H, H2, J2-4 = 1.6 Hz), 7.87 (dd, 1H, H4, J4-5 = 8.8 Hz, J2-4 = 1.6 Hz), 6.63 (d, 1H, H5, J4-5 = 8.8 Hz), 3.31 (s, 2H, NH2).
13C NMR (CDCl3, 100 MHz): δ (ppm) 191.15, 164.46, 155.78, 137.39, 123.92, 109.99.
Reference: [1] Patent: WO2018/209132, 2018, A1, . Location in patent: Paragraph 0458; 0489
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 292 - 300
[3] Patent: US2009/143420, 2009, A1, . Location in patent: Page/Page column 7
[4] Patent: EP1724263, 2006, A1, . Location in patent: Page/Page column 55
[5] Patent: EP3305785, 2018, A1, . Location in patent: Paragraph 0177; 0178
  • 2
  • [ 22790-82-5 ]
  • [ 69879-22-7 ]
Reference: [1] Doklady Akademii Nauk SSSR, 1949, vol. 65, p. 843[2] Chem.Abstr., <1949> 6626,
  • 3
  • [ 24424-99-5 ]
  • [ 69879-22-7 ]
  • [ 199296-40-7 ]
YieldReaction ConditionsOperation in experiment
93% With dmap; triethylamine In dichloromethane at 20℃; To a stirring solution of (Boc)20 (1.75 g, 8 mmol) in DCM (10 mL)was added the suspension of 6-aminonicotinaldehyde SM 1 (488 mg, 4 mmol), DMAP (25 mg, 0.2 mmol) and Et3N(1.2 g, 12 mmol) in DCM (20 mL) at RT and stirred overnight. The reaction mixture was concentrated and the residue was diluted with H20 and extracted with DCM. Combined organicextracts were dried over anhydrous Na2504 and concentrated under reduced pressure to obtain cmde product, which was purified by silica gel column chromatography eluting with 50percent EtOAc in PE to afford compound 1(1.2 g, 93percent) as white solid. LC-MS: m/z = 123.0 [M+H-BOC]
Reference: [1] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 747
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