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[ CAS No. 253801-04-6 ] {[proInfo.proName]}

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Product Details of [ 253801-04-6 ]

CAS No. :253801-04-6 MDL No. :MFCD06738280
Formula : C8H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :YJKMYHNMBGQQQZ-UHFFFAOYSA-N
M.W : 146.15 Pubchem ID :21250644
Synonyms :

Calculated chemistry of [ 253801-04-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.48
TPSA : 45.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.69
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.43 mg/ml ; 0.00977 mol/l
Class : Soluble
Log S (Ali) : -1.71
Solubility : 2.88 mg/ml ; 0.0197 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.213 mg/ml ; 0.00146 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 253801-04-6 ]

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

Application In Synthesis of [ 253801-04-6 ]

* 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 [ 253801-04-6 ]
  • Downstream synthetic route of [ 253801-04-6 ]

[ 253801-04-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 253801-04-6 ]
  • [ 74626-47-4 ]
Reference: [1] Synlett, 2011, # 15, p. 2223 - 2227
  • 2
  • [ 53857-57-1 ]
  • [ 68-12-2 ]
  • [ 253801-04-6 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.416667 h;
Stage #2: With sec.-butyllithium In tetrahydrofuran; cyclohexane at -70 - -60℃; for 2 h;
A) Preparation of Intermediate Products; Intermediate Product 1: 1H-indazole-5-carbaldehyde; 2.60 g (65.00 mmol) sodium hydride (60percent in mineral oil) was added batchwise to a solution of 11.64 g (59.08 mmol) 5-bromo-1H-indazole in 150 mL THF under argon within 10 minutes and the mixture was stirred for 15 minutes at RT. The reaction mixture was cooled to -70° C. and within 30 minutes 100.00 mL (130.00 mmol) sec-butyllithium (1.3 M in cyclohexane) were added dropwise, while the temperature was kept below -60° C. The mixture was stirred for a further 2 h at -70° C. and then a solution of 20.00 mL (0.260 mol) DMF in 20 mL THF was added dropwise, while the temperature was kept below -50° C. The reaction mixture was slowly heated to RT and stirred for 16 h. Then the mixture was slowly cooled to 0° C. and slowly 180 mL of 2N aqueous HCl was added dropwise, the mixture was stirred for a further 15 minutes and the pH was adjusted to 9-10 with sat. aqueous sodium bicarbonate solution. The aqueous phase was exhaustively extracted with EtOAc, the combined org. phases were dried over magnesium sulphate and evaporated down i. vac. Column chromatography (silica gel, petroleum ether/EtOAc 1:1 v/v), trituration with hexane and drying i. vac. at 50° C. yielded the product. Yield: 4.40 g (51percent of theory) Rf=0.37 (silica gel, petroleum ether/EtOAc 1/1 v/v) ESI-MS: (M+H)+=147
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4482 - 4485
[2] Patent: WO2005/84672, 2005, A1, . Location in patent: Page/Page column 40-41
[3] Patent: US2005/227968, 2005, A1, . Location in patent: Page/Page column 15-16
[4] Patent: WO2008/154241, 2008, A1, . Location in patent: Page/Page column 67
  • 3
  • [ 53857-57-1 ]
  • [ 253801-04-6 ]
YieldReaction ConditionsOperation in experiment
57%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25 h;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran; hexane at -40 - 20℃; for 1.5 h;
1H-INDAZOLE-5-CARBALDEHYDE (57) To a solution of commercially available 5- bromoindazole (0.5 g, 2.53 mmol) in dry THF (10 ml) was added 2.5 M solution of n-BuLi in hexane (6.42 mmol) at-40 C and under argon atmosphere. After 15 minute of stirring at this temperature, DMF (0.4 ml, 5.06 mmol) was added and the mixture stirred for additional 30 minutes AT-40 C. The cold bath was then removed and the mixture was allowed to stir for one hrs at room temeperature. Water (30 ml) was added and the aqueous layer was extracted with EtOAc (2X30 ml). The organic layer was washed with brine, dried (NA2S04) and concentrated to give 0.54 g of crude 57 that was purified on silica gel to give 0.21 g (57percent yield) aldehyde 57. 'H NMR (400 MHz, CDCL3) : 8 7.62 (dd, 1H), 7.98 (d, 1H), 8.35 (M, 2H), 10.11 (s, 1H), 10. 59 (br. S, 1H) ppm.
Reference: [1] Patent: WO2005/813, 2005, A1, . Location in patent: Page 36
[2] Patent: US6313110, 2001, B1,
  • 4
  • [ 68-12-2 ]
  • [ 253801-04-6 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 1 h;
Stage #2: at -78 - 20℃; for 2.5 h;
Stage #3: With water In tetrahydrofuran
Example 1; Synthesis of 4-(lH-indazol-5-yl)-6-(4-phenoxyphenyl)pwimidin-2(lH)-one; STEP 1:; [0198] lH-indazole-5-carbaldehyde (2). w-Butyllithium (35.0 mL, 87.5 mmol) was added slowly to 5-bromoindazole (1, 4.98 g, 25.3 mmol) in THF (60 mL) at -780C. After 30 min, the solution was warmed to -4O0C over 30 min and then cooled to -780C. DMF (3.1 mL, 77.5 mmol) was added. After 15 min, the reaction flask was removed from the dry ice/acetone bath and stirred at room temperature for 2.5 h. The solution was quenched with H2O. The aqueous layer was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered and concentrated to a golden oil. The crude material was purified by column chromatography (0-100percent EtOAc/hexanes) to give 2 as a light yellow solid (1.91 g, 52percent yield). LCMS m/z 147.0 (MH+), R, 1.53 min.[0199] Reference for the synthesis of lH-indazole-5-carbaldehyde: E. Piatnitski, WO 2005/000813 p 37.
Reference: [1] Patent: WO2007/124288, 2007, A1, . Location in patent: Page/Page column 50
  • 5
  • [ 201230-82-2 ]
  • [ 55919-82-9 ]
  • [ 141-53-7 ]
  • [ 253801-04-6 ]
YieldReaction ConditionsOperation in experiment
59% at 110℃; for 6 h; A mixture of 5-iodoindazole (10 g, 41 mmol) , HCOONa (5.57 g, 82 mmol) and PdCI2(PPh3J2 (1.44 g, 2.05 mmol) in DMF (60 mL) was put under vacuum and charged with carbon monoxide (CO). This process was repeated three times, after which the mixture was kept at 110 0C for 6 hr. After cooling to room temperature (rt), the reaction mixture was diluted with brine and extracted with EtOAc. The organic phases were combined, washed with brine, dried, and concentrated. The crude product was purified by column chromatography to afford 1 H-indazole-5-carboxaldehyde (3.52 g, 59percent) as a white solid.
Reference: [1] Patent: WO2008/71451, 2008, A1, . Location in patent: Page/Page column 47
  • 6
  • [ 74626-47-4 ]
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Reference: [1] Patent: US6200978, 2001, B1,
  • 7
  • [ 88990-57-2 ]
  • [ 253801-04-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5442 - 5447
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