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Chemical Structure| 437998-34-0
Chemical Structure| 437998-34-0
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Product Details of [ 437998-34-0 ]

CAS No. :437998-34-0 MDL No. :MFCD18389343
Formula : C7H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :LBTYNQNVZNPATH-UHFFFAOYSA-N
M.W : 215.05 Pubchem ID :22931092
Synonyms :

Calculated chemistry of [ 437998-34-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.64
TPSA : 69.11 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 1.36
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 0.94
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.922 mg/ml ; 0.00429 mol/l
Class : Soluble
Log S (Ali) : -2.41
Solubility : 0.829 mg/ml ; 0.00386 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.701 mg/ml ; 0.00326 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 437998-34-0 ]

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 [ 437998-34-0 ]

* 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 [ 437998-34-0 ]
  • Downstream synthetic route of [ 437998-34-0 ]

[ 437998-34-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 20776-51-6 ]
  • [ 437998-34-0 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6 h; Inert atmosphere Step A: To 2-amino-3-bromobenzoic acid (0.5 g, 2.3 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (0.46 g, 3.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.53 g, 2.8 mmol), ammonium chloride (0.5 g, 9.7 mmol), and diisopropylethylamine (1.7 ml, 9.7 mmol). The mixture was purged with N2 and stirred for 6 h. The mixture was poured into water and extracted with EtOAc (3.x.50 mL). The combined extracts were washed with brine (2.x.20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was treated with DCM (10 mL) resulting in a precipitate which was collected by filtration and dried to afford 2-amino-3-bromobenzamide as a pale pink solid (0.42 g, 84percent). LCMS (ESI) m/z 215/217 (M+H)+
83%
Stage #1: With ammonium chloride; benzotriazol-1-ol In N,N-dimethyl-formamide at 0 - 20℃; for 0.0833333 h; Inert atmosphere
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.333333 h; Inert atmosphere
Stage #3: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere
A 100 mL round bottom flask with stir bar was charged with 30 (Combi-Blocks, 0.500 g, 3.0 mmol, 1 eq) and NH4Cl (0.486 g, 9.1 mmol, 3 eq).
The flask was evacuated and back-filled with Ar (*3). Anh. DMF (15 mL) was added, and the mixture was cooled to 0° C. with stirring. 1-hydroxybenzotriazole hydrate (0.449 g, 3.3 mmol, 1.1 eq) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.636 g, 3.3 mmol, 1.1 eq) 5 min later.
After 20 min N,N-diisopropylethylamine was added.
The reaction was stirred at 0° C. to room temperature overnight.
The reaction was diluted with NaHCO3 (aq, sat) and extracted with EtOAc (*2).
The combined EtOAc fractions were washed with water (*2), brine (*1), and dried over Na2SO4.
The solids were filtered off, and the volatiles were removed via rotary evaporation.
The resulting solid was triturated with 20percent DCM/hexanes, and the solids were collect via vacuum filtration. 0.409 g (2.5 mmol, 83percent yield) of 31 was collected as an off-white solid.
Reference: [1] Patent: US2012/53174, 2012, A1, . Location in patent: Page/Page column 49
[2] Patent: US2016/168140, 2016, A1, . Location in patent: Paragraph 1000
[3] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
[4] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 235 - 252
  • 2
  • [ 331646-98-1 ]
  • [ 437998-34-0 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
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