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[ CAS No. 279255-90-2 ] {[proInfo.proName]}

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Chemical Structure| 279255-90-2
Chemical Structure| 279255-90-2
Structure of 279255-90-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 279255-90-2 ]

CAS No. :279255-90-2 MDL No. :MFCD09834884
Formula : C14H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XIMLBZMOOXHPJQ-UHFFFAOYSA-N
M.W : 247.29 Pubchem ID :21865484
Synonyms :

Calculated chemistry of [ 279255-90-2 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.27
TPSA : 51.46 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) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.74
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.26 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.196 mg/ml ; 0.000791 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.159 mg/ml ; 0.000641 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 279255-90-2 ]

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 [ 279255-90-2 ]

* 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 [ 279255-90-2 ]
  • Downstream synthetic route of [ 279255-90-2 ]

[ 279255-90-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
83% at 0 - 20℃; for 3 h; To a solution of tert-butyl 5-formyl-1H-indo . g, 12.23 mmol) in methanol (30 mL) was added sodium tetrahydroborate (0.463 g, 12.23 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 3 hours then overnight at room temperature. The resulting solution was diluted with water (40 mL), then extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum to afford tert-butyl 5-(hydroxymethyl)-1H-indole-1- carboxylate (2.5 g, 10.11 mmol, 83percent yield) as a yellow oil. LCMS m/z = 270.3 [M+Na]+.
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 6847 - 6850
[2] Patent: WO2017/216726, 2017, A1, . Location in patent: Page/Page column 955
  • 2
  • [ 335649-83-7 ]
  • [ 279255-90-2 ]
Reference: [1] Patent: WO2006/86255, 2006, A2, . Location in patent: Page/Page column 67
  • 3
  • [ 15893-47-7 ]
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
  • [ 879887-21-5 ]
  • [ 879887-65-7 ]
YieldReaction ConditionsOperation in experiment
11% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 8 h; D-Leucinamide (1.0 g, 6.0 mmol), 1-(t-butyloxycarbonyl)-5-formylindole (Example 1, 1.23 g, 5.0 mmol) and DCE (15 mL) were mixed at room temperature. Sodium triacetoxyborohydride (1.48 g, 7.0 mmol) was added in one portion with vigorous stirring. After 2 h, another portion (0.15 g, 0.7 mmol) was added and stirring was continued for an additional 6 h. The reaction mixture was diluted with a saturated NaHCO3 solution (10 mL). Three extractions with EtOAc, washing the combined organic layers with brine, drying over Na2SO4 and filtration provided a solution. Removal of solvent in vacuo afforded an oil. Column chromatography (DCM:MeOH:95:5) provided three fractions, after removal of solvent in vacuo: (1) 1-(t-Butyloxycarbonyl)-5-hydroxymethylindole (162 mg, 11percent yield, Rf=0.5): 1H NMR (CDCl3, 300 MHz): 8.11 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.54 (s, 1H), 7.31 (dd, 1H, J=8,2), 6.55 (d, 1H, J=3), 4.75 (s, 2H), 1.69 (s, 9H); (2) 2R-bis-(1-t-butyloxycarbonylindol-5-ylmethyl)amino-4-methylpentanamide BMS594447 (382 mg, 12percent yield, Rf=0.4): 1H NMR (CDCl3, 300 MHz): 8.1 (d, 2H, J=8), 7.61 (d, 2H, J=2), 7.52 (s, 2H), 7.31 (dd, 2H, J=8,2), 6.62 (m, 1H), 6.56 (d, 2H, J=4), 6.05 (br s, 1H), 3.85 (d, 2H, J=16), 3.66 (d, 2H, J=16), 3.35 (m, 1H), 1.69 (s, 18H), 0.96 (d, 3H, J=7), 0.87 (d, 3H, J=7); MS (ES+): 589.4 (C35H45N3O5) and (3) the title product (986 mg, 55percent yield, Rf=0.3): 1H NMR (CDCl3, 300 MHz): 8.10 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.49 (d, 1H, J=1), 7.28-7.20 (m, 3H), 6.55 (d, 1H, J=4), 3.93 (d, 1H, J=16), 3.77 (d, 1H, J=16), 3.28-3.20 (m, 1H), 1.69 (s, 9H), 0.94 (d, 3H, J=7), 0.85 (d, 3H, J=7); MS (ES+): 360 (C20H30N3O3, M++H).
Reference: [1] Patent: US2006/63799, 2006, A1, . Location in patent: Page/Page column 7
  • 4
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
Reference: [1] Patent: US6492394, 2002, B1,
  • 5
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
Reference: [1] Patent: US6492394, 2002, B1,
  • 6
  • [ 24424-99-5 ]
  • [ 279255-90-2 ]
Reference: [1] Patent: WO2005/18557, 2005, A2,
  • 7
  • [ 33140-84-0 ]
  • [ 279255-90-2 ]
Reference: [1] Patent: WO2005/18557, 2005, A2,
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