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[ CAS No. 885272-46-8 ] {[proInfo.proName]}

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Chemical Structure| 885272-46-8
Chemical Structure| 885272-46-8
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Product Details of [ 885272-46-8 ]

CAS No. :885272-46-8 MDL No. :MFCD08059277
Formula : C13H16BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DUZIJTYKDFFQDJ-UHFFFAOYSA-N
M.W :298.18 Pubchem ID :51650745
Synonyms :

Calculated chemistry of [ 885272-46-8 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.08
TPSA : 29.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.29
Log Po/w (XLOGP3) : 3.39
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 3.19
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 3.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.89
Solubility : 0.0386 mg/ml ; 0.00013 mol/l
Class : Soluble
Log S (Ali) : -3.69
Solubility : 0.061 mg/ml ; 0.000204 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.03
Solubility : 0.0281 mg/ml ; 0.0000942 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.56

Safety of [ 885272-46-8 ]

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 [ 885272-46-8 ]

* 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 [ 885272-46-8 ]
  • Downstream synthetic route of [ 885272-46-8 ]

[ 885272-46-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 86626-38-2 ]
  • [ 885272-46-8 ]
YieldReaction ConditionsOperation in experiment
74% at 20℃; A mixture of above obtained 4-bromoindoline (759 mg, 3.81 mmol), and (Boc)20 (976 mg, 4.48 mmol) in MeCN (8 mL) was stirred at room temperature overnight. After evaporated, the residue was dissolved in ethyl acetate (40 mL), washed with water (3 x 20 mL) and brine (1 x 20 mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177(840 mg, 74percent>) as a white solid. 1H-NMR (400 MHz. DMSO-<3/4) δ 1.50 (s, 9H), 3.02 (t, J= 8.8 Hz, 2H), 3.94 (t, J = 8.8 Hz, 2H), 7.12 (m, 2H), 7.56 (m, 1H).
74% at 20℃; A mixture of above obtained 4-bromoindoline (759 mg, 3.81 mmol), and (Boc)2O (976 mg, 4.48 mmol) in MeCN (8 mL) was stirred at room temperature overnight. After evaporated, the residue was dissolved in ethyl acetate (40 mL), washed with water (3×20 mL) and brine (1×20 mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 (840 mg, 74percent) as a white solid. 1H-NMR (400 MHz. DMSO-d6) δ 1.50 (s, 9H), 3.02 (t, J=8.8 Hz, 2H), 3.94 (t, J=8.8 Hz, 2H), 7.12 (m, 2H), 7.56 (m, 1H).
74% at 20℃; Obtained above in MeCN (8mL) 4- bromo-indoline (759mg, 3.81mmol) and the mixture of (Boc) 2O (976mg, 4.48mmol) was stirred at room temperature overnight. After evaporation, the residue was dissolved in ethyl acetate (40 mL), washed with water (3 × 20 mL) and brine (1x20mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 as a white solid (840 mg, 74percent).
62.5% With dmap In dichloromethane at 20℃; for 48 h; To a solution of 4-bromoindoline (12.2 g, 61.6 mmol) in dichloromethane (200 mL) was added Boc20 (14.8 g, 67.8 mmol) and DMAP (0.75 g, 6.16 mmol). The mixture was stirred at room temperature for 48 h and then evaporated. The residue was purified by silica gel column chromatography with EtOAc in hexanes (0 to 10percent gradient) to provide the title compound (11.5 g, 62.5percent). 1H NMR (CDC13) δ: 7.80 (br. s, 1H), 6.98-7.12 (m, 2H), 4.00 (t, J=8.7 Hz, 2H), 3.08 (t, J=8.7 Hz, 2H), 1.50-1.66 (s, 9H).

Reference: [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 225
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0566
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0481
[4] Patent: WO2016/25933, 2016, A2, . Location in patent: Page/Page column 185
  • 2
  • [ 99365-48-7 ]
  • [ 885272-46-8 ]
Reference: [1] Patent: WO2011/130628, 2011, A1,
[2] Patent: JP2015/187145, 2015, A,
[3] Patent: US2013/102595, 2013, A1,
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