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[ CAS No. 439811-37-7 ] {[proInfo.proName]}

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Chemical Structure| 439811-37-7
Chemical Structure| 439811-37-7
Structure of 439811-37-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 439811-37-7 ]

CAS No. :439811-37-7 MDL No. :MFCD04114991
Formula : C17H22BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :CJXZBFPDZDHCJT-UHFFFAOYSA-N
M.W : 368.27 Pubchem ID :22890526
Synonyms :

Calculated chemistry of [ 439811-37-7 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.53
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 94.01
TPSA : 46.61 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.55
Log Po/w (XLOGP3) : 3.64
Log Po/w (WLOGP) : 3.9
Log Po/w (MLOGP) : 2.96
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 3.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.29
Solubility : 0.019 mg/ml ; 0.0000515 mol/l
Class : Moderately soluble
Log S (Ali) : -4.31
Solubility : 0.0182 mg/ml ; 0.0000493 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.54
Solubility : 0.0106 mg/ml ; 0.0000289 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.34

Safety of [ 439811-37-7 ]

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 [ 439811-37-7 ]

* 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 [ 439811-37-7 ]
  • Downstream synthetic route of [ 439811-37-7 ]

[ 439811-37-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 746550-66-3 ]
  • [ 24424-99-5 ]
  • [ 439811-37-7 ]
YieldReaction ConditionsOperation in experiment
100% With water; sodium carbonate In tetrahydrofuran at 20℃; for 2 h; Step 1. 4-(4-Bromobenzoyl)-piperidine-1-carboxylic acid tert-butyl ester. [00596] To a 250 mL R. B. flask was charged with (4-bromophenyl)-piperidin-4- yl-methanone (5 g, 20 mmol), THF (30 mL), water (30 mL), Na2CO3 (10 g, 90 mmol), and di-t-butyldicarbonate (4.35 g, 20.0 mmol). The reaction mixture was stirred at rt for 2 h and partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc and the combined organics was washed with brine, dried, filtered, and evaporated to produce 4-(4-bromobenzoyl)-piperidine-1-carboxylic acid t-butyl ester, 7.1 g (100percent).
74.5% at 20℃; for 2 h; Step 1 : To a solution of (4-bromophenyl)(piperidin-4-yl)methanone (600 mg, 2.23 mmol) in MeOH (5 mL) was added (Boc)20 (561 mg, 2.57 mmol). The reaction mixture was stirred for 2 h at rt and concentrated. The residues was recrystallized from methanol to give tert-butyl 4- (4-bromobenzoyl)piperidine-l-carboxylate (650 mg, 74.5percent, LC-MS 98percent) as a solid. NMR (400 MHz, DMSO-< ) S (ppm): 7.94 (d, J= 8.4 Hz, 2H), 7.78 (d, J= 8.8 Hz, 2H), 3.82-3.59 (m, 3H), 3.02 (bs, 2H), 1.92 (bs, 2H), 1.75 (bm, 2H),T .46 (bs, 9H); MS (ESI) m/z 370 [C17H22BrN03+2†.
74.5% at 20℃; for 2 h; To a solution of (4-bromophenyl)(piperidin-4-yl)methanone (600 mg, 2.23 mmol) in MeOH (5 mL) was added (Boc)2O (561 mg, 2.57 mmol).
The reaction mixture was stirred for 2 h at rt and concentrated.
The residues was recrystallized from methanol to give tert-butyl 4-(4-bromobenzoyl)piperidine-1-carboxylate (650 mg, 74.5percent, LC-MS 98percent) as a solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.94 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.8 Hz, 2H), 3.82-3.59 (m, 3H), 3.02 (bs, 2H), 1.92 (bs, 2H), 1.75 (bm, 2H), 1.46 (bs, 9H); MS (ESI) m/z 370 [C17H22BrNO3+2]+.
Reference: [1] Patent: WO2016/205590, 2016, A1, . Location in patent: Paragraph 00596
[2] Patent: WO2013/147711, 2013, A1, . Location in patent: Page/Page column 231
[3] Patent: US2014/371199, 2014, A1, . Location in patent: Paragraph 0801
[4] Patent: US2005/54628, 2005, A1, . Location in patent: Page/Page column 23-24
[5] Patent: US2005/49269, 2005, A1, . Location in patent: Page/Page column 12; 21
  • 2
  • [ 1046478-89-0 ]
  • [ 1122-91-4 ]
  • [ 439811-37-7 ]
YieldReaction ConditionsOperation in experiment
66% With caesium carbonate In 1,4-dioxane at 110℃; Inert atmosphere Compound B6.1 (1.00 g; 2.721 mmol), 4-bromobenzaldehyde (0.604 g;3.266 mmol) and cesium carbonate (0.436 ml; 5.443 mmol) weresuspended in dry 1,4-dioxane (10.0 mL) under argon atmosphere. The mixture was heated to 110 °C and stirred overnight at this temperature. The reaction mixture was cooled to room temperature, quenched with water (30 mL) and extracted with MTB-ether. The combined organic layerswere washed with 5percent citric acid solution, saturated NaHCO3 solution and brine, dried with sodium sulfate, filtered by suction and evaporated to dryness. The solid residue was triturated with petrolether/MTB-ether (1:1), filtered by suction, washed with petrolether/MTB-ether (3:1) and dried.From the filtrate further product was isolated by flash chromatography (Companion RF; 40 g Si50 silica gel column). Yield: 657 mg (66percent) colorless solid; LC/MS (A), Rt: 2.72 mm; (M+H-t-Bu) 312.0/314.0
Reference: [1] Organic Letters, 2014, vol. 16, # 11, p. 3064 - 3067
[2] Patent: WO2017/76484, 2017, A1, . Location in patent: Page/Page column 58
  • 3
  • [ 79099-07-3 ]
  • [ 439811-37-7 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 11, p. 3064 - 3067
[2] Patent: WO2017/76484, 2017, A1,
  • 4
  • [ 203186-01-0 ]
  • [ 439811-37-7 ]
Reference: [1] Patent: WO2016/205590, 2016, A1,
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