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[ CAS No. 22721-16-0 ] {[proInfo.proName]}

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Chemical Structure| 22721-16-0
Chemical Structure| 22721-16-0
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Product Details of [ 22721-16-0 ]

CAS No. :22721-16-0 MDL No. :MFCD07439747
Formula : C8H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SIAWPBGFCFNHCS-UHFFFAOYSA-N
M.W :230.06 Pubchem ID :16463261
Synonyms :

Calculated chemistry of [ 22721-16-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.41
TPSA : 49.33 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) : -5.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 3.57
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 1.57
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0406 mg/ml ; 0.000176 mol/l
Class : Soluble
Log S (Ali) : -4.29
Solubility : 0.0118 mg/ml ; 0.0000511 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.196 mg/ml ; 0.000851 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.43

Safety of [ 22721-16-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22721-16-0 ]

* 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.

  • Downstream synthetic route of [ 22721-16-0 ]

[ 22721-16-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 119-68-6 ]
  • [ 22721-16-0 ]
YieldReaction ConditionsOperation in experiment
With chloroform; bromine
With bromine; acetic acid
  • 2
  • [ 22721-16-0 ]
  • [ 108-24-7 ]
  • [ 860732-60-1 ]
YieldReaction ConditionsOperation in experiment
With (R)-10-camphorsulfonic acid; acetic acid
  • 3
  • [ 22721-16-0 ]
  • [ 541-41-3 ]
  • [ 22721-17-1 ]
YieldReaction ConditionsOperation in experiment
for 20h; Heating;
YieldReaction ConditionsOperation in experiment
Rk. mit NH3 -> 5-Brom-2-methylamino-benzoesaeureamid;
Rk. mit Chlorameisensaeureethylester -> 6-Brom-1,2-dihydro-1-methyl-4H-3,1-benzoxazindion-(2,4);
YieldReaction ConditionsOperation in experiment
N-Methyl-anthranilsaeure, Br2 (Eisessig);
(yield)57percent;
2-Methylamino-benzoesaeure, Brom, Nitrobenzol;
  • 6
  • [ 22721-16-0 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 860732-60-1 ]
  • 7
  • [ 717866-13-2 ]
  • [ 22721-16-0 ]
  • [ 717866-09-6 ]
YieldReaction ConditionsOperation in experiment
With HATU; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; 22.e (E). N- {1-ACETYL-2, 2, 4-trimethyl-4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-1,2,3, 4- tetrahydro-quinolin-6-yl}-5-bromo-2-methylamino-benzamide; General procedure C To a solution of the compound described in example 22d (132 mg), 5-bromo-2-methylamino benzoic acid (101 mg) and DIPEA (255 PI) in CH2Cl2 (3 ML) was added HATU (166 mg) at room temperature. The reaction mixture was stirred for 18 h at room temperature. Ethyl acetate (15 ml) and 2 M aqueous NAOH (15 ml) were added. The organic layer was separated and washed with 2 M aqueous NAOH (10 ml) and water (15 ml), dried and concentrated in vacuo. The title compound was purified by preparative HPLC (method A). Yield: 69.8 mg; MS-ESI: [M+H] += 663.4 ; HPLC : Rt = 14. 65 min (method 3).
  • 8
  • [ 371-71-1 ]
  • [ 22721-16-0 ]
  • [ 50736-90-8 ]
YieldReaction ConditionsOperation in experiment
50-70 In acetonitrile in presence of NaF, 20°C, 20 min;
50-70 In acetonitrile in presence of NaF, 20°C, 20 min;
  • 10
  • [ 610-71-9 ]
  • [ 593-51-1 ]
  • [ 22721-16-0 ]
  • 11
  • [ 22721-16-0 ]
  • [ 917-61-3 ]
  • 6-bromo-1-methylquinazoline-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: 2-(methylamino)-5-bromobenzoic acid; sodium isocyanate With acetic acid In water at 40℃; for 0.5h; Stage #2: With sodium hydroxide In water at 40 - 70℃; for 1.16667h; 31.2; 49.2 Step 2: 2-(cyanomethyl)-5-hydroxybenzonitrile. To a stirred mixture of 5-bromo-2- (methylamino) benzoic acid (280.00 mg, 1.217 mmol, 1.00 equiv) in AcOH/H2O (16.00 mL, 1/50) at room temperature under air atmosphere was added NaOCN (112.00 mg, 1.723 mmol, 1.42 equiv) at room temperature. The resulting mixture was stirred for additional 30 min at 40 oC. To the above mixture was added NaOH (1.38 g, 0.035 mmol, 0.03 equiv) in portions over 10 min at 40 oC. The resulting mixture was stirred for additional 1 h at 70 oC. The reaction was monitored by LCMS. The resulting mixture was cooled down to room temperature and was diluted with water (50 mL). The mixture was acidified to pH 6 with aq. HCl (1 M). The resulting mixture was extracted with EtOAc (30 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase Flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 um, 120 g; Eluent A: water (plus 10 mmol/L NH4HCO3); Eluent B: ACN; Gradient: 30% - 50% B in 30 min; Flow rate: 60 mL/min; Detector: 220/254 nm; desired fractions were collected at 42% B and concentrated under reduced pressure to afford 6-bromo-1-methyl-3H-quinazoline-2,4-dione (50 mg, 16%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.71 (s, 1H), 8.05 (d, J = 2.5 Hz, 1H), 7.92 (dd, J = 8.9, 2.5 Hz, 1H), 7.41 (d, J = 9.0 Hz, 1H), 3.43 (s, 3H). LC/MS (ESI, m/z): [(M + 18)]+ = 254.75, 256.75.
  • 12
  • [ 50-00-0 ]
  • [ 5794-88-7 ]
  • [ 22721-16-0 ]
YieldReaction ConditionsOperation in experiment
85% With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 31.1; 49.1 Step 1: 5-Bromo-2-(methylamino)benzoic acid To a stirred mixture of 5-bromoanthranilic acid (2.00 g, 9.258 mmol, 1.00 equiv) and (HCHO)n (0.83 g, 27.667 mmol, 2.99 equiv) in DMF (20.00 mL) were added HOAc (5.58 g, 92.919 mmol, 10.04 equiv) and NaBH3CN (1.76 g, 28.007 mmol, 3.03 equiv) at room temperature. The resulting mixture was stirred for 6 h at room temperature. The resulting mixture was diluted with water (60 mL) and extracted with EtOAc (3 x 50 mL). The combined organic phase was dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase Flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 mm, 330 g; Eluent A: water (plus 10 mmol/L FA); Eluent B: ACN; Gradient: 30% - 50% B in 25 min; Flow rate: 80 mL/min; Detector: 220/254 nm; desired fractions were collected at 42% B and concentrated under reduced pressure to afford 5-bromo-2- (methylamino)benzoic acid (1.8 g, 85%) as a white solid. LC/MS (ESI, m/z): [(M + 1)]+ = 230.00, 232.00.
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