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[ CAS No. 2941-58-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2941-58-4
Chemical Structure| 2941-58-4
Chemical Structure| 2941-58-4
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Product Details of [ 2941-58-4 ]

CAS No. :2941-58-4 MDL No. :MFCD08459026
Formula : C8H6BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :YNONWDJSSPJFBQ-UHFFFAOYSA-N
M.W : 244.11 Pubchem ID :11218765
Synonyms :

Calculated chemistry of [ 2941-58-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.81
TPSA : 50.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.77
Log Po/w (WLOGP) : 3.07
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 3.78
Consensus Log Po/w : 3.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.0148 mg/ml ; 0.0000606 mol/l
Class : Moderately soluble
Log S (Ali) : -4.52
Solubility : 0.00736 mg/ml ; 0.0000301 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.96
Solubility : 0.027 mg/ml ; 0.000111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.35

Safety of [ 2941-58-4 ]

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 [ 2941-58-4 ]

* 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 [ 2941-58-4 ]
  • Downstream synthetic route of [ 2941-58-4 ]

[ 2941-58-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 28611-39-4 ]
  • [ 2941-58-4 ]
  • [ 10205-71-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 5, p. 1450 - 1458
  • 2
  • [ 143-33-9 ]
  • [ 2941-58-4 ]
  • [ 943-03-3 ]
Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, # 9, p. 1561 - 1562
  • 3
  • [ 773837-37-9 ]
  • [ 2941-58-4 ]
  • [ 943-03-3 ]
Reference: [1] Synlett, 2009, # 16, p. 2682 - 2684
  • 4
  • [ 151-50-8 ]
  • [ 2941-58-4 ]
  • [ 943-03-3 ]
Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, # 9, p. 1561 - 1562
  • 5
  • [ 1747-60-0 ]
  • [ 2941-58-4 ]
YieldReaction ConditionsOperation in experiment
95% With nitrous acid isobutyl ester; copper(ll) bromide In acetonitrile at 65℃; for 4 h; Inert atmosphere Dry copper (II) bromide (2.70 g, 11.6 mmol), isobutyl nitrite (2 mL, 15.0 mmol) andWas added to acetonitrile (150 mL) at room temperature under an argon atmosphere, and then a solution of 6-methoxybenzo [d] thiazol-2-amine (1.80 g, 9.99 mmol) in acetonitrile (50 mL) . The resulting mixture was heated to 65 ° C. and stirred for 4 hours under an argon atmosphere while maintaining this temperature.The reaction mixture was allowed to cool to room temperature, 2 M hydrochloric acid (30 mL) was added, and the mixture was extracted with chloroform (3 × 150 mL). The combined organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel 200 g; hexane: ethyl acetate (2: 1)) to give 2-bromo-6-methoxybenzo [d] thiazole (2.32 g, yield 95percent) as a red-brown solid. The measured physical properties of the product are as follows
89% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 80℃; for 2 h; 39.1.1)
2-bromo-6-methoxy-1,3-benzothiazol-2-amine
20 g (111 mmol) of 6-methoxy-1,3-benzothiazol-2-amine is solubilized in 400 ml of acetonitrile, then 13.2 ml (III mmol; 1 equivalent) of tert-butyl nitrite and 29 g (130 mmol; 1.2 equivalent) of CuBr2 are added to the reaction medium which is then maintained under stirring at 80° C. for 2 hours.
The solvent is evaporated off under reduced pressure, then the residue is taken up in 250 ml of ethyl acetate and washed twice with 200 ml of water.
The organic phase is dried over sodium sulphate, then the solvent is evaporated off under reduced pressure and 24 g (yield=89percent) of 2-bromo-6-methoxy-1,3-benzothiazol-2-amine is obtained and is used without other purification in to the following stage.
MS-LC: MH+=243.98; r.t.=10.89 min.
85% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 80℃; for 2 h; Compound 4 (500 mg, 2.77 mmol) in acetonitrile (15 mL) to dissolve was then, t-butylnitrite (286 mg, 2.77 mmol) and CuBr2 (744 mg, 3.33 It was added mmol) and stirred for 2 hours at 80 ° C. After checking thecompletion of the reaction, then cooled at room temperature, then evaporated under reduced pressure to remove the solvent. Theconcentrated residue was extracted with ethyl acetate (10 ml) and water (8 ml). After the extracted organic layer was filtered anddried over anhydrous magnesium sulfate, and distilled under reduced pressure of the filtrate. As a result, the 5 compound (574 mg,yield: 85percent) was obtained.
84% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; To a solution of copper (II) bromide (0.74 g, 3.33 mmol) in acetonitrile (12.5 mL) at 0 0C was added t-butylnitrite (0.495 mL, 4.16 mmol). To this mixture was added 2- amino-6-methoxybenzothiazole (0.5 g, 2.77 mmol) portion- wise via an addition funnel. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered through a pad of Celite.(R). and the Celite.(R). pad was washed with diethyl ether, followed by ethyl acetate. The filtrate was washed with IN hydrochloric acid, followed by brine, dried over magnesium sulfate, filtered and concentrated to afford 0.57 g (84percent) of 2-bromo-6-(methyloxy)-l,3-benzothiazole. 1H NMR (400 MHz, DMSO-J6): δ 7.85 (d, J = 9 Hz, IH), 7.68 (d, J = 3 Hz, IH), 7.10 (dd, J = 9, 3 Hz, IH), 3.80 (s, 3H).
78% With copper(I) bromide; isopentyl nitrite In acetonitrile at 65℃; for 3 h; Inert atmosphere To a solution of copper bromide (7.4 g, 0.0336 mol) and polyethylene glycol (14 g) in acetonitrile (150 mL) was added isoamyl nitrite (4.9 g, 0.042 mol) portionwise at room temperature. A solution of 6-methoxybenzo[b]thiazol-2-amine (5 g, 0.028 mol) in acetonitrile (100 mL) was then added dropwise to the mixture under nitrogen over a period of 10 minutes. The mixture was then stirred at 65 °C for 3 hours. After being cooled to room temperature, the mixture was poured into a 20percent aq. hydrochloric acid solution (200 mL) and organics were extracted with dichloromethane (3 x 50 mL). The organic layers were washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography [petroleum ether/ethyl acetate=15: l] to give compound B-120 (5.3 g, 78percent yield) as a white solid. LCMS: (ES+) m/z (M+H)+ =244.0, tR=0.820.
62% With tert.-butylnitrite; copper(ll) bromide In acetonitrile for 3 h; To a black solution of Copper (II) bromide (149 mg, 0.666 mmol) in Acetonitrile(1 mL) was added t-Butyl nitrite (0.095 mL, 0.72 1 mmol) at room temperature followedby 6-methoxybenzo[d]thiazol-2-amine (100mg, 0.555 mmol). Immediate bubbling and amild exotherm was observed upon benzothiazole addition. After 3 hours, the reactionmixture was diluted with EtOAc and washed with 1.0 M HC1, saturated NaHCO3, andthen Brine. The organic phase was dried over Mg504, filtered and concentrated to areddish-brown solid. The crude material was purified by ISCO flash chromatography (0-15percent EtOAc/Hex over 20 mm, 12 g silica gel cartridge, Product at 5percent). The desiredfractions were combined and concentrated to yield Intermediate 253A (84 mg, 0.344mmol, 62.0 percent yield) as an off-white solid. LC-MS. Method H, RT = 1.12 mm, MS (ESI)m/z: 244.0, 246.0 (M+H). ‘H NMR (400MHz, CHLOROFORM-d) 7.89 (d, J9.0 Hz,1H), 7.28 (1H under CDC13), 7.09 (dd, J9.0, 2.6 Hz, 1H), 3.90 (s, 3H)
12% With tert.-butylnitrite; copper(I) bromide In acetonitrile for 3 h; 6- Methoxybenzo[d]thiazol-2-amine (5.0 g; 27.7 mmol) was dissolved in 125 mL CH3CN. t- Butylnitrite (3.4 mL; 28 mmol) was added slowly. CuBr (5.0 g; 34.9 mmol) was added portion-wise through a funnel. The reaction was monitored by HPLC. After 3 hours, ethyl acetate (500 mL) was added, and the mixture was filtered through celite. The organic layer was washed with brine twice (200 mL each). The organic layer was dried over MgS04. After filtration, the solvent was removed. The residual was dissolved in 50 mL CH2CI2, and 2 g of silica gel was added. After drying, the silica gel loaded on a silica gel cake in hexane. The product was eluted with 5percent ethyl acetate and 95percent hexane. A yellowish band was collected (1.5 L). The solvent was removed to afford 0.81 g product. Yield 12percent. 1H NMR (400 MHz; CD3COCD3), δ 7.95 (d, 3JHH = 8.9 Hz, 1H, Ar-H), 7.61 (d, 4JHH = 2.6 Hz, 1H, NH), 7.13 (dd, 3JHH = 9.0 Hz, 4JHH = 2.6 Hz, 1H, Ar-H), 3.89 (s, 3H, OCH3).

Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 27, p. 9330 - 9337
[2] Patent: JP6095208, 2017, B2, . Location in patent: Paragraph 0027; 0028; 0029
[3] Patent: US2009/275624, 2009, A1, . Location in patent: Page/Page column 22
[4] Chemical Communications, 2016, vol. 52, # 75, p. 11199 - 11202
[5] Patent: KR101659952, 2016, B1, . Location in patent: Paragraph 0219; 0221
[6] Patent: WO2009/5998, 2009, A1, . Location in patent: Page/Page column 118
[7] Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, # 9, p. 1561 - 1562
[8] Synlett, 2009, # 16, p. 2682 - 2684
[9] Patent: WO2015/66371, 2015, A1, . Location in patent: Paragraph 00240-00241
[10] Tetrahedron Letters, 2003, vol. 44, # 47, p. 8535 - 8537
[11] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 676; 677
[12] Patent: WO2013/40183, 2013, A1, . Location in patent: Paragraph 0061
[13] Patent: WO2008/89933, 2008, A2, . Location in patent: Page/Page column 19
  • 6
  • [ 1747-60-0 ]
  • [ 7787-70-4 ]
  • [ 2941-58-4 ]
Reference: [1] Patent: US5371093, 1994, A,
  • 7
  • [ 1747-60-0 ]
  • [ 110-46-3 ]
  • [ 440123-48-8 ]
  • [ 2941-58-4 ]
YieldReaction ConditionsOperation in experiment
14% With hydrogenchloride In acetonitrile a.
2-Bromo-6-methoxy-benzothiazole
To a solution containing dry Copper (11) bromide (2.68 g, 12 mmol), tri(ethylene glycol) dimethyl ether (5 g) in acetonitrile (150 mL) was added isoamyl nitrite (2 mL, 15 mmol).
Reaction was stirred at room temp under nitrogen for 30 min.
To this suspension was added, dropwise, a solution (obtained by sonification) containing 2-amino-6-methoxy-benzothiazole (1.8 g, 10 mmol) and tri(ethylene glycol) dimethyl ether (5 g) in acetonitrile (50 mL).
Reaction was stirred at room temp for 10 min, and then heated to 50° C. for 3 hr.
Reaction was cooled to room temp, poured cautiously into aqueous 6M hydrochloric acid and extracted with ethyl acetate.
Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo.
Residue was crystallized from ether/hexane (1:10) yielding the title compound (1.48 g, 61percent) MH+=244
Supernatant solution was concentrated, dried under vacuum yielding 2,7-dibromo-6-methoxy-benzothiazole (0.45 g, 14percent) as a yellow solid. MH+=322
Reference: [1] Patent: US2004/102435, 2004, A1,
  • 8
  • [ 2941-58-4 ]
  • [ 808755-67-1 ]
YieldReaction ConditionsOperation in experiment
99% With boron tribromide In dichloromethane at 20℃; for 7 h; Inert atmosphere 2-Bromo-6-methoxybenzo [d] thiazole (555 mg, 2.28 mmol) was dissolved in methylene chloride (10 mL) at room temperature under an argon atmosphere. To the resulting solution, 1 M boron tribromide methylene chloride solution (4 mL) was added at room temperature. The resulting mixture was stirred under an argon atmosphere at room temperature for 7 hours.The reaction mixture was added to ice water and then extracted with chloroform (3 × 30 mL). The combined organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel 80 g; hexane: ethyl acetate (3: 1)) to give 2-bromobenzo [d] thiazol-6-ol (521 mg, yield 99 percent) As a brown solid. The measured physical properties of the product are as follows.
83%
Stage #1: With boron tribromide In dichloromethane
Stage #2: With water In dichloromethane at 20℃; for 2 h;
2-bromo-6- methoxybenzo[d]thiazole (0.90 g; 3.7 mmol) was dissolved in CH2CI2 (50 mL). BBr3 (1M in CH2C12, 16 mL, 16 mmol) was added slowly. White precipitate formed immediately. After overnight, HPLC showed complete conversion. Excess CH2CI2 (200 mL) and brine (100 mL) were added. White precipitate formed immediately. The mixture was stirred at RT for 2 hours, until most solid dissolved. The organic layer was separated, and aqueous layer extracted with 2 x 100 mL CH2CI2. The combined organic solution was dried over MgS04. The solvent was removed to afford 0.71 g of product. Yield 83percent.
Reference: [1] Patent: JP6095208, 2017, B2, . Location in patent: Paragraph 0030; 0031; 0032
[2] Chemistry - A European Journal, 2016, vol. 22, # 27, p. 9330 - 9337
[3] Patent: WO2013/40183, 2013, A1, . Location in patent: Paragraph 0062
[4] Patent: WO2016/161572, 2016, A1, . Location in patent: Page/Page column 50
[5] Patent: WO2004/108663, 2004, A1, . Location in patent: Page 100
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