[ CAS No. 105679-22-9 ] {[proInfo.proName]}

Name: 105679-22-9|7-Bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine|96%
Brand: Ambeed
SKU: A116061
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Quality Control of [ 105679-22-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105679-22-9 ]

SDS Specification

Alternatived Products of [ 105679-22-9 ]

Product Details of [ 105679-22-9 ]

CAS No. :	105679-22-9	MDL No. :	MFCD09056750
Formula :	C₈H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JLZUUGCTPRPFKZ-UHFFFAOYSA-N
M.W :	214.06	Pubchem ID :	18008960
Synonyms :

Calculated chemistry of [ 105679-22-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.76
TPSA :	21.26 Å²

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) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	2.34
Log Po/w (WLOGP) :	1.68
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	2.53
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.05
Solubility :	0.193 mg/ml ; 0.000902 mol/l
Class :	Soluble
Log S (Ali) :	-2.43
Solubility :	0.803 mg/ml ; 0.00375 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0539 mg/ml ; 0.000252 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.07

Safety of [ 105679-22-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 105679-22-9 ]

* 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 [ 105679-22-9 ]
Downstream synthetic route of [ 105679-22-9 ]

[ 105679-22-9 ] Synthesis Path-Upstream 1~6

1
[ 38191-34-3 ]
[ 106-93-4 ]
[ 105679-22-9 ]

Reference： [1] Patent: WO2016/49099, 2016, A1, . Location in patent: Page/Page column 94

2
[ 280142-79-2 ]
[ 105679-22-9 ]

Reference： [1] Patent: US6632814, 2003, B1, . Location in patent: Page/Page column 334

3
[ 321436-06-0 ]
[ 105679-22-9 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4700 - 4704

4
[ 27684-84-0 ]
[ 105679-22-9 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597

5
[ 38191-34-3 ]
[ 105679-22-9 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597

6
[ 105679-22-9 ]
[ 73183-34-3 ]
[ 1361110-64-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2688 - 2701
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597

[ 105679-22-9 ] Synthesis Path-Downstream 1~34

2
[ 105679-22-9 ]
[ 6160-65-2 ]
[ 1000802-47-0 ]

Yield	Reaction Conditions	Operation in experiment
58%		INTERMEDIATE 31; 7-Bromo-2,3-dihydro-benzo[l,4]oxazine-4-carbothioic acid amide; A solution of Intermediate 19 (1.O g, 4.7 mmol) in THF (1OmL) was added to thiocarbonyldiimidazole (1.2 g, 5.8 mmol) and the mixture heated to 12O0C under microwave irradiation for 20 minutes. After cooling to r.t., it was poured into methanolic ammonia (1OmL of a 7M solution, 70 mmol) and stirred at r.t. over the weekend. It was concentrated in vacuo, and the residue triturated with water and Et2O followed by IM hydrochloric acid and Et2O to give the title compound (0.75 g, 58%) as a cream solid. 5H (DMSO-d6) 4.16-4.35 (4H, m), 7.07 (IH, dd, J 8.9, 2.3 Hz), 7.15 (IH, d, J2.3 Hz), 7.39 (IH, d, J 8.9 Hz). LCMS (ES+) 275 (M+H)+.

Reference： [1]Patent: WO2008/44022,2008,A1 .Location in patent: Page/Page column 34
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4700 - 4704

3
[ 280142-79-2 ]
[ 105679-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium hydroxide; water; at 50℃; for 2h;	Reference Example 12[0516] 7-Bromo-3,4-dihydro-2H-benzo[1,4]oxazine[0517] A solution of 4-acetyl-7-bromo-3,4-dihydro-2H-benzo[1,4]oxazine (9.5 g, Reference Example 13) in methanol (200 ml) was treated with aqueous sodium hydroxide (50 ml, 3M) was stirred at 50[deg.] C. for 2 hours. The mixture was evaporated to low bulk, then diluted with water (100 ml) and then extracted three times with dichloromethane (200 ml). The combined extracts were dried over magnesium sulphate then evaporated to give the title compound (6.0 g) as a brown oil.

Reference： [1]Patent: US6632814,2003,B1 .Location in patent: Page/Page column 334

4
[ 105679-22-9 ]
[ 6160-65-2 ]
C₁₂H₁₀BrN₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation;	A mixture of 7-bromo-3,4-dihydro-2H-benzo[l,4]oxazine (7.07 g, 33.00 mmol) and l,l '-thiocarbonyldiimidazole (8.86 g, 49.70 mmol) in TetaF (83 mL) was heated to 1200C under microwave irradiation, in a sealed tube, for 20 minutes, and then cooled to r.t. NH3 (110 mL, 7N solution in MeOH, 770 mmol) was added. The reaction mixture was stirred at r.t. for 16 h, and then concentrated in vacuo. The residue was triturated with IM aqueous HCl, then Et2O, water and again Et2O, and then dried in vacuo to give the title compound (5.31 g, 59%) as a cream solid. deltaH (DMSO-d6) 8.66-7.53 (2H, m), <n="62"/>7.39 (IH, d, J 8.7 Hz), 7.15 (IH, d, J2.3 Hz), 7.07 (IH, dd, J8.9 and 2.3 Hz), 4.30-4.20 (4H, m). LCMS (ES+) 272.9 and 274.9 (M+H)+, RT 3.12 minutes {Method T).

Reference： [1]Patent: WO2008/47109,2008,A1 .Location in patent: Page/Page column 60-61

5
[ 321436-06-0 ]
[ 105679-22-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4700 - 4704

6
[ 105679-22-9 ]
potassium trifluoro(6-(3-methoxy-2,2-dimethyl-3-oxopropoxy)pyridin-3-yl)borate [ No CAS ]
[ 1246212-31-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In ethanol; water; at 70℃; for 0.75h;Inert atmosphere; Microwave irradiation; sealed vial;	SECTION B: Preparation of example compounds Scheme B1 : Preparation of example B-4Intermediate B-2: methyl 3-(5-{3,4-dihydro-2W-benzo[ib][1,4]oxazin-7- yl)pyridin-2-yloxy)-2,2-dimethylpropanoate -step b17-Bromo-3,4-dihydro-2/+benzo[<;b][1 ,4]oxazine B-1 (44.9 mg, 0.197 mmol), potassium trifluoro(6-(3-methoxy-2,2-dimethyl-3-oxopropoxy)pyridin-3- yl)borate A-8 (80.0 mg, 0.256 mmol), anhydrous potassium carbonate (68.3 mg, 0.492 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3- chloropyridyl)paadium(ll) dichloride (PEPPSl-ZPr, 13.6 mg, 0.020 mmoi) were mixed in 1 :1 ethanol:water (1.97 mi_) in a 5 mi_ microwave reactor vial, evacuated several times and placed under an argon atmosphere. The reaction mixture was sealed, heated at 70 0C for 45 mins under microwave irradiation, then cooled to room temperature and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give methyl 3-(5-(3f4-dihydro-2H-benzo[6][1 f4]oxazin-7-yl)pyridin-2-yloxy)-2,2- dimethylpropanoate B-2 (39.2 mg, Yield=58%). MS (ESI) [M+1]+ 343.

Reference： [1]Patent: WO2010/107765,2010,A1 .Location in patent: Page/Page column 64

7
[ 105679-22-9 ]
[ 1228147-50-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2688 - 2701

8
[ 105679-22-9 ]
[ 73183-34-3 ]
[ 1361110-64-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2688 - 2701
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597

9
[ 615-18-9 ]
[ 105679-22-9 ]
[ 1245708-11-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 544 - 549

10
[ 27684-84-0 ]
[ 105679-22-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597

11
[ 38191-34-3 ]
[ 105679-22-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597

12
[ 105679-22-9 ]
[ 1571111-33-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597

13
[ 105679-22-9 ]
[ 1571111-32-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 592 - 597

14
[ 105679-22-9 ]
[ 6279-86-3 ]
ethyl 9-bromo-7-hydroxy-5-oxo-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate [ No CAS ]