[ CAS No. 169044-96-6 ] {[proInfo.proName]}

Name: 169044-96-6|Methyl 2-amino-5-bromo-4-methoxybenzoate|95%
Brand: Ambeed
SKU: A216747
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Quality Control of [ 169044-96-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 169044-96-6 ]

SDS Specification

Alternatived Products of [ 169044-96-6 ]

Product Details of [ 169044-96-6 ]

CAS No. :	169044-96-6	MDL No. :	MFCD21868787
Formula :	C₉H₁₀BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SFXCMXLNSVHKCE-UHFFFAOYSA-N
M.W :	260.08	Pubchem ID :	19701951
Synonyms :

Calculated chemistry of [ 169044-96-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.32
TPSA :	61.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
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) :	2.18
Log Po/w (XLOGP3) :	2.31
Log Po/w (WLOGP) :	1.83
Log Po/w (MLOGP) :	1.77
Log Po/w (SILICOS-IT) :	1.69
Consensus Log Po/w :	1.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.244 mg/ml ; 0.00094 mol/l
Class :	Soluble
Log S (Ali) :	-3.24
Solubility :	0.149 mg/ml ; 0.000574 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.208 mg/ml ; 0.000798 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.76

Safety of [ 169044-96-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 169044-96-6 ]

* 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 [ 169044-96-6 ]

[ 169044-96-6 ] Synthesis Path-Downstream 1~18

1
[ 50413-30-4 ]
[ 169044-96-6 ]

Yield	Reaction Conditions	Operation in experiment
82.06%	With bromine; In dichloromethane; at 20℃; for 20h;	To a solution of compound 34 (4.0 g, 0.02 mol) in DCM(200 mL) was added bromine (1.36 mL, 0.02 mol). Themixture was stirred at room temperature for 20 h. It wasdiluted with saturated sodium hydrogen sulfite (50 mL) andthe aqueous solution was extracted with DCM. The combinedorganic layers were washed with brine, dried overNa2SO4 and filtered. The residue was purified by silica gelcolumn chromatography eluting with PE/EA to give whitepowder 35 (4.71 g, 82.06%). 35: 1H NMR delta (400 MHz,CDCl3) 8.04 (s, 1H), 6.14 (s, 1H), 5.87 (s, 2H), 3.89 (s, 3H),3.87 (s, 3H).
	With bromine; In chloroform; at 0 - 20℃;	A-8a (15.0 g, 82.8 mmol, LO equiv.) is dissolved in chloroform (750 mL) and cooled to 0 C. A solution of bromine (4.2 mL, 82.8 mmol, 1.0 equiv.) in chloroform (10 mL) is added dropwise and the reaction mixture stirred for 1 h at rt. Then the reaction mixture is quenched with sodium thiosulphate (aqu.) and extracted with EtOAc. The combined organic layer is washed with saturated NaHC03 solution, dried over Na2S04 and concentrated in vacuo. The crude product is washed with hexane to give the final compound A-9b (HPLC method: GVK_LCMS_05: tret [min] = 1 .76; [M+H]+ = 260.0).

Reference： [1]Medicinal Chemistry Research,2018,vol. 27,p. 1851 - 1862
[2]Patent: WO2018/115380,2018,A1 .Location in patent: Page/Page column 87

2
[ 169044-96-6 ]
[ 77287-34-4 ]
[ 950577-05-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With ammonium formate; at 165℃; for 18.0h;	A solution of <strong>[169044-96-6]methyl 2-amino-5-bromo-4-methoxybenzoate</strong> (75 mg, 0.29 mmol) and ammonium formate (38 mg, 0.8 mmol) in formamide (1 mL) was heated at 165 C for 18h. The mixture was allowed to cool to room temperature then diluted with an excess of water. The solid formed was collected by filtration and washed with water then ethyl acetate and dried to give 6-bromo-7-methoxyquinazolin-4(3H)-one (53 mg, 72% yield) as a pale yellow solid. MS (EI) for C9H7BrN2O2: 255, 257 (MH+).

Reference： [1]Patent: WO2010/135524,2010,A1 .Location in patent: Page/Page column 190

3
[ 169044-96-6 ]
[ 16712-16-6 ]
[ 77287-34-4 ]
[ 950577-05-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 165℃; for 18.0h;	Reagent Preparation 1; [00451] STEP I : A solution of methyl 2-amino-5-bromo-4- mcthoxybenx.oaie (75 nig. 0.29 mmol) and ammonium formate (38 mg, 0.8 mmol ) in formamide ( I inL) was heated at 165 "C for 18li. The mixture was allowed to cool to room temperature then dilulcd with an excess of waler. The solid formed was collected by filtration aiul washed with water then cihyl acctaic and dried to give 6-broirK>-7-mcthox yquinazolin- (3/-A)-onc (53 mg, 72% yield) as a pale yellow sol id. MS (EI) for 255, 257 ( IT1).

Reference： [1]Patent: WO2012/71519,2012,A1 .Location in patent: Page/Page column 198

4
[ 169044-96-6 ]
[ 1256955-27-7 ]

Reference： [1]Patent: WO2012/71519,2012,A1

5
[ 169045-04-9 ]
[ 74-88-4 ]
[ 169044-96-6 ]

Yield	Reaction Conditions	Operation in experiment
5.5 g	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.0h;	Step 2: Methyl 2-amino-5-bromo-4-methoxybenzoateTo a stirred suspension of <strong>[169045-04-9]2-amino-5-bromo-4-methoxybenzoic acid</strong> (6.3 g, 0.025 mol) and potassium carbonate (7.06 g, 0.051 mol) in N,ll-dimethyl formamide (63 mL) was added methyl iodide (5.45 g, 0.038 mol) dropwise at 0C. After the addition was complete, the reaction mixture was stirred at room temperature for 1 h. The mixture was poured into ice cold water (500 mL) and extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water (100 mL) followed by brine solution, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using column chromatography (100-200 mesh silica gel, 20% EtOAc in hexane) to afford the title compound as white solid (5.5 g, 83% yield). *H NMR (400 MHz, DMSO-d6) : delta 7.78 (s, 1H), 6.85 (brs, 2H), 6.44 (s, 1H), 3.80 (s, 3H), 3.75 (s, 3H). ESI-MS: Calculated mass: 258.98; Observed mass: 258.3 [M-H]

Reference： [1]Patent: WO2014/169167,2014,A1 .Location in patent: Page/Page column 87; 88

6
[ 4294-95-5 ]
[ 169044-96-6 ]

Reference： [1]Patent: WO2014/169167,2014,A1
[2]Medicinal Chemistry Research,2018,vol. 27,p. 1851 - 1862

7
[ 169044-96-6 ]
6-bromo-2,4-dichloro-7-methoxyquinazoline [ No CAS ]

Reference： [1]Patent: WO2014/169167,2014,A1

8
[ 169044-96-6 ]
4-(6-bromo-2-chloro-7-methoxy-4,4a-dihydroquinazolin-4-yl)morpholine [ No CAS ]

Reference： [1]Patent: WO2014/169167,2014,A1

9
[ 169044-96-6 ]
N-(3-(2-chloro-7-methoxy-4-morpholinoquinazolin-6-yl)-2-fluorophenyl)-3-fluoropropane-1-sulfonamide [ No CAS ]

Reference： [1]Patent: WO2014/169167,2014,A1

10
[ 169044-96-6 ]
N-(3-(2-(2-aminopyrimidin-5-yl)-7-methoxy-4-morpholinoquinazolin-6-yl)-2-fluorophenyl)-3-fluoropropane-1-sulfonamide [ No CAS ]

Reference： [1]Patent: WO2014/169167,2014,A1

11
[ 590-28-3 ]
[ 169044-96-6 ]
6-bromo-7-methoxyquinazoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In water; acetic acid; at 20 - 50℃; for 24.0h;	Step 3: 6-Bromo-7-methoxyquinazoiine-2,4( lH,3H)-dioneTo a stirred suspension of <strong>[169044-96-6]methyl 2-amino-5-bromo-4-methoxybenzoate</strong> (5.5 g, 0.021 mol) in acetic acid (25 mL) was added 0.1 M aqueous solution of potassium cyanate (7.49 g, 0.10 mol) dropwise at room temperature. The reaction mixture was stirred at 50C for 24 h. The solid separated was filtered, washed with water (20 mL) followed by 10% EtOAc in hexane (50 mL) and dried under vacuum to afford the corresponding urea.To the stirred suspension of the above urea in methanol (20 mL) was added 2N sodium hydroxide (10 mL). The reaction mixture was stirred at 90C for 1 h. The mixture was cooled to room temperature, acidified with 3M hydrochloric acid to pH 3. The solid obtained was filtered and dried under vacuum to afford the title compound as white solid (3.5 g, 61% yield). *H NMR (400 MHz, DMSO-d6) : delta 11.29 (s, 1H), 11.18 (S, 1H), 7.94 (S, 1H), 6.74 (s, 1H), 3.90 (s, 3H).

Reference： [1]Patent: WO2014/169167,2014,A1 .Location in patent: Page/Page column 88

12
[ 169044-96-6 ]
2-amino-4-methoxy-5-(isopentenyl)benzoicacid [ No CAS ]