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[ CAS No. 21344-24-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 21344-24-1
Chemical Structure| 21344-24-1
Chemical Structure| 21344-24-1
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Product Details of [ 21344-24-1 ]

CAS No. :21344-24-1 MDL No. :MFCD18254753
Formula : C7H4BrNS Boiling Point : -
Linear Structure Formula :- InChI Key :YMOORGYWRBQPDZ-UHFFFAOYSA-N
M.W : 214.08 Pubchem ID :12885487
Synonyms :

Calculated chemistry of [ 21344-24-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.32
TPSA : 41.13 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) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.89
Log Po/w (WLOGP) : 3.06
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 3.87
Consensus Log Po/w : 2.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0475 mg/ml ; 0.000222 mol/l
Class : Soluble
Log S (Ali) : -3.41
Solubility : 0.0825 mg/ml ; 0.000386 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0317 mg/ml ; 0.000148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 21344-24-1 ]

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 [ 21344-24-1 ]

* 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 [ 21344-24-1 ]
  • Downstream synthetic route of [ 21344-24-1 ]

[ 21344-24-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 21344-28-5 ]
  • [ 21344-24-1 ]
YieldReaction ConditionsOperation in experiment
53% With copper(ll) bromide; isopentyl nitrite In acetonitrile at 20℃; Example 16E
5-Bromothieno[2,3-b]pyridine
The product of Example 16D (1.35 g. 9.0 mmol) was treated with iso-amylnitrite (Aldrich. 2.10 g. 18.0 mmol) and CuBr2 (Aldrich, 4.03 g. 18.0 mmol) in MeCN (20 mL) at ambient temperature overnight.
The reaction mixture was quenched with saturated NH4Cl (20 mL) and then extracted with EtOAc (3*50 mL).
The combined extracts were washed with brine (2*30 mL) and concentrated.
The residue was purified with chromatography (SiO2, EtOAc/hexane, v. 80/20.
Rf=0.80) to give the title compound (1.03 g, yield, 53.0percent).
1H NMR (300 MHz, CDCl3) 8 ppm 7.22 (d, J=6.10 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H).
8.21 (d, J=2.37 Hz, 1H), 8.61 (d, J=2.0(3 Hz, 1H):MS (DCI/NH3) m/z 214 (M+1)+, 216 (M+1)+.
Reference: [1] Patent: US2008/153860, 2008, A1, . Location in patent: Page/Page column 25
[2] Journal of Heterocyclic Chemistry, 1968, vol. 5, p. 773 - 778
  • 2
  • [ 1242336-81-7 ]
  • [ 21344-24-1 ]
YieldReaction ConditionsOperation in experiment
60% at 150℃; (C) To a solution of 971 5-bromothieno[2,3-b]pyridine-2-carboxylic acid (6.6 g, 25.6 mmol) in 973 DMA (50 mL) was added 974 DBU (12.8 g, 84.1 mmol) and the resulting mixture was stirred at 150° C. overnight. After cooling to rt, the reaction was quenched with 444 H2O (100 mL) and the resulting mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (0-10percent EtOAc/petroleum ether) to afford 975 5-bromothieno[2,3-b]pyridine (3.3 g, 60percent), as a white solid. LC/MS: mass calcd. for C7H4BrNS: 212.92, found: 213.8, 215.8 [M+H, M+H+2]+.
Reference: [1] Patent: US2017/291908, 2017, A1, . Location in patent: Paragraph 0760
  • 3
  • [ 56267-50-6 ]
  • [ 2065-75-0 ]
  • [ 21344-24-1 ]
YieldReaction ConditionsOperation in experiment
3% With hydrogenchloride In ethanol at 105℃; for 24 h; Inert atmosphere To a solution of tert-butyl thiophen-2-ylcarbamate (3.0 g, 15 mmol) and 2-bromomalonaldehyde (2.57 g, 17 mmol) in EtOH (30 mL) was added concentrated HC1 (7.5 mL) under N2. The reaction mixture was heated to 105 oC for 24 h. After cooling to rt, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 2percent MeOH in DCM to give 5-bromothieno[2,3-b]pyridine as a yellow solid (90 mg, 3percent). 1H NMR (300 MHz, CDC13 8.60 (d, J = 2.1 Hz, 1H), 8.11 (d, J = 2.4 Hz, 1H), 7.55-7.60 (m, 1H), 7.19-7.22 (m, 1H). LC-MS (ESI) mlz 215 (M+H)+.
Reference: [1] Patent: WO2015/31613, 2015, A1, . Location in patent: Paragraph 000171
  • 4
  • [ 21344-35-4 ]
  • [ 21344-24-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1968, vol. 5, p. 773 - 778
  • 5
  • [ 21344-24-1 ]
  • [ 73183-34-3 ]
  • [ 1034579-02-6 ]
Reference: [1] Patent: WO2010/118207, 2010, A1, . Location in patent: Page/Page column 284-285
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