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[ CAS No. 1035235-27-8 ]

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Chemical Structure| 1035235-27-8
Chemical Structure| 1035235-27-8
Structure of 1035235-27-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1035235-27-8 ]

CAS No. :1035235-27-8 MDL No. :MFCD10700130
Formula : C13H16BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BFCZVUVSPUKWET-UHFFFAOYSA-N
M.W :298.18 g/mol Pubchem ID :49853504
Synonyms :

Calculated chemistry of [ 1035235-27-8 ]

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 : 74.52
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) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.25
Log Po/w (XLOGP3) : 2.87
Log Po/w (WLOGP) : 3.02
Log Po/w (MLOGP) : 2.92
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.56
Solubility : 0.0821 mg/ml ; 0.000275 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.211 mg/ml ; 0.000708 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 : 2.31

Safety of [ 1035235-27-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1035235-27-8 ]

* 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 [ 1035235-27-8 ]
  • Downstream synthetic route of [ 1035235-27-8 ]

[ 1035235-27-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 923590-95-8 ]
  • [ 24424-99-5 ]
  • [ 1035235-27-8 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine In tetrahydrofuran at 10 - 20℃; for 12 h; Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10°C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20°C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 χ 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75percent). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) δ ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).
Reference: [1] Patent: WO2017/158388, 2017, A1, . Location in patent: Page/Page column 55; 214
[2] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7576 - 7582
  • 2
  • [ 24424-99-5 ]
  • [ 1035235-27-8 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In N,N-dimethyl-formamide at 20℃; for 18 h; A solution of 4-bromoisoindoline hydrochloride (1.40 g, 5.97 mmol) in DMF (30 mL) was treated with triethylamine (2.50 mL, 17.9 mmol) and di-tert-butyl dicarbonate (2.08 mL, 8.95 mmol), and the mixture was stirred at room temperature for 18 h. Themixture was diluted with EtOAc (65 mL) and washed three times with saturated aqueousNaHCO3. The organic phase was dried and concentrated. The residue was subjected tocolumn chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-3 0percent), to provide tert-butyl 4-bromoisoindoline-2-carboxylate as a white solid (1.70 g,91percent yield).
Reference: [1] Patent: WO2016/65236, 2016, A1, . Location in patent: Page/Page column 118
  • 3
  • [ 127168-81-4 ]
  • [ 24424-99-5 ]
  • [ 1035235-27-8 ]
Reference: [1] Patent: US2008/171754, 2008, A1, . Location in patent: Page/Page column 104
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