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[ CAS No. 112253-70-0 ] {[proInfo.proName]}

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Chemical Structure| 112253-70-0
Chemical Structure| 112253-70-0
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Product Details of [ 112253-70-0 ]

CAS No. :112253-70-0 MDL No. :MFCD12674809
Formula : C7H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :OFXMSVAQRRUVHA-UHFFFAOYSA-N
M.W : 215.05 Pubchem ID :13805507
Synonyms :

Calculated chemistry of [ 112253-70-0 ]      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) : -7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 0.41
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 0.94
Consensus Log Po/w : 0.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.77
Solubility : 3.66 mg/ml ; 0.017 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 8.03 mg/ml ; 0.0373 mol/l
Class : Very 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 : 1.24

Safety of [ 112253-70-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 112253-70-0 ]

* 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 [ 112253-70-0 ]
  • Downstream synthetic route of [ 112253-70-0 ]

[ 112253-70-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 112253-70-0 ]
  • [ 122-51-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
71% With trifluoroacetic acid In ISOPROPYLAMIDE at 160℃; for 0.5 h; Microwave radiation To a solution of 2-amino-4-bromo-benzamide (1 equiv) in DMA (0.14 M) were added triethyl orthoformate (10 equiv) and trifluoroacetic acid (1 equiv). The reaction vessel was sealed and exposed to microwave radiation (160 0C, medium absorption setting) for 30 minutes. The reaction mixture was concentrated in vacuo and the residue was filtered through a silica pad with 10 percent methanol in ethyl acetate yielding the required product as a pale yellow solid. <n="121"/>7-Bromo-3H-quinazolin-4-one: (71 percent yield, 100 percent purity) m/z (LC-MS, ESP): 268 [M+H]+ R/T = 2.94 min
Reference: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 119-120
  • 2
  • [ 67-56-1 ]
  • [ 112253-70-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
80% at 130℃; for 2 h; Microwave irradiation; Inert atmosphere 2-Amino-4-bromobenzamide (107 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent,Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 80percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0085; 0086; 0087; 0088
  • 3
  • [ 112253-70-0 ]
  • [ 109-94-4 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
84% With sodium methylate In ethanol for 1.5 h; Heating / reflux 2) 4-Bromoanthranilic amide (40 g, 186 mmol) obtained in 1) was dissolved in ethanol (400 mL). Thereto was added sodium methoxide (54.2 g, 93 mmol) with stirring under ice-cooling and then ethyl formate (60.1 mL, 744 mmol) was added dropwise. The mixture was heated under reflux for 1.5 hrs. The reaction mixture was allowed to cool to room temperature and water (500 mL) was added and then acetic acid (40 mL) was added. The mixture was concentrated under reduced pressure and water (200 mL) was added. The precipitate was collected by filtration and dried to give 7-bromo-3H-quinazolin-4-one (35 g, 156 mmol, 84percent). 7-bromo-3H-quinazolin-4-one [0153] 1H NMR (DMSO-d6) δ ppm: 7.68 (dd, J=1.7, 8.5 Hz, 1H), 7.88 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 8.14 (s, 1H).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 32
  • 4
  • [ 20776-50-5 ]
  • [ 112253-70-0 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: With ammonia In water; N,N-dimethyl-formamide at 20℃; for 15 h;
Compound 37 (9.3 g, 43.1 mmol), HOBT (13.4 g, 99 mmol) and EDC.HC1 (19 g, 99 mmol) were dissolved in DMF (40 mL). The solution was stirred at 20°C for 30 minutes. To the solution, H3.H2O (20 mL). was slowly added The reaction mixture was stirred for 15 hours at room temperature. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL). The mixture was washed with saturated NaHC03 and H4CI aqueous solution. The organic layer was dried over Na2S04 and concentrated under vacuum to give the compound 38 (6.2 g, 67percent yield).
53% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 25℃; for 18.5 h; Inert atmosphere To a solution of 2-amino-4-bromobenzoic acid (10g, 46.3 mmol) in tetrahydrofuran (THF) (10 mL) was added HOBT (16.30 g, 106 mmol) and EDC (20.41 g, 106 mmol). The mixture was stirred at 25 °C for 30 min when ammonia (30 mL, 1386 mmol) was added to the solution. The mixture was stirred at 25 °C for 18 hr. The solvent was removed in vacuo when EtOAc (200 mL) was added to the mixture. The organic phase was washed with NaHC03 (aq, 100 mL X 3) and dried with NaS204. The solvent was removed to afford 2-amino-4-bromobenzamide (5.5g, 24.55 mmol, 53 percent yield).
40% With ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 20℃; for 24 h; To a solution of 2-amino-4-bromobenzoic acid (1 equiv) in DMA (0.23 M), were added ammonium chloride (7 equiv), HBTU (1 equiv) and diisopropylethylamine (2 equiv). The reaction mixture was stirred for 24 hours at room temperature. DMA was evaporated and the residue was purified by flash column chromatography onto silica gel eluting with a gradient of TBME/hexane to yield the desired product as a white solid. 2-Amino-4-bromo-benzamide: 40 percent yield, 100 percent purity) m/z (LC-MS, ESP): 215 [M+H]+ R/T = 3.00 min
Reference: [1] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 48
[2] Patent: WO2017/98440, 2017, A1, . Location in patent: Page/Page column 120
[3] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 119
[4] Patent: WO2011/75699, 2011, A2, . Location in patent: Page/Page column 206
[5] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
  • 5
  • [ 1152237-09-6 ]
  • [ 112253-70-0 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With tin(ll) chloride In ethyl acetate for 0.333333 h; Reflux
Stage #2: With sodium hydroxide In ethyl acetate
Stage #3: Acidic conditions
Synthesis of 3:A mixture of 2 (2.0 g, 10.6 mmol) in EtOAc (200 mL) was treated with SnCl2 (9.4 g, 42 mmol) at reflux for 20 min. After addition of 1N NaOH, the formed solid was filtered and washed with EtOAc. The organic phase was separated. The aqueous phase was neutralized (pH7) and extracted with EtOAc (2.x.70 mL). The combined organic extracts were concentrated to provide 3 (1.53 g, 67percent) as a tan solid.
Reference: [1] Patent: US2010/160314, 2010, A1, . Location in patent: Page/Page column 69
  • 6
  • [ 79603-03-5 ]
  • [ 112253-70-0 ]
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 31-32
  • 7
  • [ 135484-83-2 ]
  • [ 112253-70-0 ]
Reference: [1] Patent: WO2012/13643, 2012, A1,
[2] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 235 - 252
  • 8
  • [ 304858-65-9 ]
  • [ 112253-70-0 ]
Reference: [1] Journal of Chemical Research, 2011, vol. 35, # 8, p. 480 - 483
[2] Patent: WO2010/56758, 2010, A1, . Location in patent: Page/Page column 118
  • 9
  • [ 76561-16-5 ]
  • [ 112253-70-0 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
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