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[ CAS No. 947249-13-0 ] {[proInfo.proName]}

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Chemical Structure| 947249-13-0
Chemical Structure| 947249-13-0
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Product Details of [ 947249-13-0 ]

CAS No. :947249-13-0 MDL No. :MFCD12405789
Formula : C6H5BrF2N2O Boiling Point : -
Linear Structure Formula :- InChI Key :KSCDCUDCOXNYJD-UHFFFAOYSA-N
M.W : 239.02 Pubchem ID :42609056
Synonyms :

Calculated chemistry of [ 947249-13-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.94
TPSA : 48.14 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.12
Log Po/w (WLOGP) : 2.88
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.9
Solubility : 0.304 mg/ml ; 0.00127 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.413 mg/ml ; 0.00173 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.32 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 947249-13-0 ]

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

Application In Synthesis of [ 947249-13-0 ]

* 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 [ 947249-13-0 ]
  • Downstream synthetic route of [ 947249-13-0 ]

[ 947249-13-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 947249-14-1 ]
  • [ 947249-13-0 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide In acetonitrile at 0℃; for 0.383333 h; To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 min at 0 °C. The reaction mixture was stirred at the same temperature for another 20 min and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93percent): NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, / = 73.6 Hz, 1H), 6.34 (s, 2H).
93% With N-Bromosuccinimide In acetonitrile at 0℃; for 0.383333 h; To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 mm at 0 °C. The reaction mixture was stirred at the same temperature for another 20 mm and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were driedover sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93percent): 1H NMR (400 MHz, DMSO-d6) ö: 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, I = 73.6 Hz, 1H), 6.34 (s, 2H).
93% With N-Bromosuccinimide In acetonitrile at 0℃; for 0.383333 h; Inert atmosphere To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 min at 0° C.
The reaction mixture was stirred at the same temperature for another 20 min and subsequently concentrated to dryness in vacuo.
The resulting viscous mass was diluted with water and extracted with ethyl acetate (3*60 mL).
The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo.
The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93percent): 1H NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, J=73.6 Hz, 1H), 6.34 (s, 2H).
91.2%
Stage #1: at 20℃; for 2 h;
Stage #2: With water; sodium hydrogencarbonate In ethyl acetate
Step 3:82 M 83To a solution of compound 82 (8.0 g, 0.05 mol) in AcOH (100 mL) was added dropwise bromine (8.0 g, 0.05 mol) at room temperature. The mixture was stirred at ambient temperature for 2 h. TLC (Petroleum ether/EtOAc 2:1 ) indicated the reaction was complete. AcOH was removed under reduced pressure and the residue was partitioned between saturated aq. NaHCO3 (200 mL) and EtOAc (200 mL). The aqueous layer was extracted with EtOAc (200 mL) and the combined organic layers were washed with brine (2*300 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give crude product, which was purified via column chromatography (petroleum ether/EtOAc 8:1-4:1 ) to afford the product 83 (10.9 g, 91.2percent) as a yellow solid.
80% With N-Bromosuccinimide In acetonitrile at 0℃; for 0.166667 h; N-Bromosuccinamide (1.00 g, 5.62 mmol) was added portionwise over 10 min to a cooled solution of 3-(difluoromethoxy)pyridin-2-amine (1.12 g) in dry acetonitrile (20 ml) at 0° C.
The reaction mixture was further stirred at 0° C. for 10 min.
The mixture was concentrated, and residue was partitioned between EtOAc/sat. Na2CO3/H2O (30 ml/15 ml/15 ml).
The organic phase was sequentially washed with sat. aqueous Na2CO3/H2O (15 ml/15 ml) and brine (30 ml), dried (Na2SO4), and concentrated.
The resulting residue was extracted with EtOAc/hexanes (6 ml/30 ml), and the resulting suspension was filtered through Celite, and the resulting filtrate was concentrated to provide 1.32 g (80percent) of 5-bromo-3-(difluoromethoxy)pyridine-2-amine. LCMS (m/z, MH+): 238.9, tR=0.52 min; 1H NMR (CDCl3, 400 MHz) δ 7.99 (d, J=2.0 Hz, 1H), 7.41 (m, 1H), 6.50 (t, J=72.8 Hz, 1H), 4.75 (br s, 2H).
80% With N-Bromosuccinimide In acetonitrile at 0℃; for 0.333333 h; Bromosuccinamide (1.0Og, 5.62 mmol) was added portionwise over 10 min to a cooled solution of 3-(difiuoromethoxy)pyridin-2-amine (1.12 g) in dry acetonitrile (20ml) at 0 0C. The reaction mixture was further stirred at 0 0C for lOmin. The mixture was concentrated, and residue was partitioned between EtO Ac/sat. Na2CO3ZH2O(S OmI/ 15ml/ 15ml). The organic phase was sequentially washed with sat. aqueous Na2CO3ZH2O(15ml/l 5ml) and brine(30ml), dried (Na2SO^, and concentrated. The resulting residue was extracted with EtOAc/hexanes(6ml/30ml), and the resulting suspension was filtered through Celite, and the resulting filtrate was concentrated to provide 1.32 g (80percent) of 5-bromo-3-(difiuoromethoxy)pyridine-2-amine. LCMS (m/z, MH+): 238.9, tR = 0.52min; 1H NMR (CDCl3, 400 MHz) δ 7.99 (d, J = 2.0 Hz, 1 H), 7.41 (m, 1 H), 6.50 (t, J = 72.8 Hz, 1 H), 4.75 (br s, 2 H).
3.2 g With N-Bromosuccinimide In acetonitrile at 0℃; for 0.383333 h; Step 3: 5-bromo-3-(difluoromethoxy)pyridin-2-amine To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 min at 0 °C. The reaction mixture was stirred at the same temperature for another 20 min and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93percent): NM (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, / = 73.6 Hz, 1H), 6.34 (s, 2H).

Reference: [1] Patent: WO2014/111496, 2014, A1, . Location in patent: Page/Page column 108; 109
[2] Patent: WO2015/91889, 2015, A1, . Location in patent: Page/Page column 74, 75
[3] Patent: US2015/175619, 2015, A1, . Location in patent: Paragraph 0221; 0222
[4] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 56
[5] Patent: US2013/210818, 2013, A1, . Location in patent: Paragraph 0416
[6] Patent: WO2009/115572, 2009, A2, . Location in patent: Page/Page column 126
[7] Patent: WO2010/100127, 2010, A1, . Location in patent: Page/Page column 73-74
[8] Patent: WO2016/142310, 2016, A1, . Location in patent: Page/Page column 75
  • 2
  • [ 6602-32-0 ]
  • [ 947249-13-0 ]
Reference: [1] Patent: US2013/210818, 2013, A1,
[2] Patent: WO2009/115572, 2009, A2,
  • 3
  • [ 947249-27-6 ]
  • [ 947249-13-0 ]
Reference: [1] Patent: US2013/210818, 2013, A1,
[2] Patent: WO2009/115572, 2009, A2,
  • 4
  • [ 1111637-77-4 ]
  • [ 947249-13-0 ]
Reference: [1] Patent: WO2014/111496, 2014, A1,
[2] Patent: WO2015/91889, 2015, A1,
[3] Patent: US2015/175619, 2015, A1,
[4] Patent: WO2016/142310, 2016, A1,
  • 5
  • [ 15128-82-2 ]
  • [ 947249-13-0 ]
Reference: [1] Patent: WO2014/111496, 2014, A1,
[2] Patent: WO2015/91889, 2015, A1,
[3] Patent: US2015/175619, 2015, A1,
[4] Patent: WO2016/142310, 2016, A1,
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