[ CAS No. 50850-93-6 ] {[proInfo.proName]}

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Quality Control of [ 50850-93-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 50850-93-6 ]

SDS Specification

Alternatived Products of [ 50850-93-6 ]

Product Details of [ 50850-93-6 ]

CAS No. :	50850-93-6	MDL No. :	MFCD00102724
Formula :	C₁₀H₁₀N₂O₂S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	VYJSGJXWKSDUSG-UHFFFAOYSA-N
M.W :	222.26	Pubchem ID :	601008
Synonyms :

Calculated chemistry of [ 50850-93-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	60.11
TPSA :	93.45 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.15
Log Po/w (XLOGP3) :	2.25
Log Po/w (WLOGP) :	2.06
Log Po/w (MLOGP) :	1.47
Log Po/w (SILICOS-IT) :	2.57
Consensus Log Po/w :	2.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.88
Solubility :	0.292 mg/ml ; 0.00131 mol/l
Class :	Soluble
Log S (Ali) :	-3.85
Solubility :	0.0315 mg/ml ; 0.000142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.177 mg/ml ; 0.000794 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 50850-93-6 ]

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

Application In Synthesis of [ 50850-93-6 ]

* 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.

Upstream synthesis route of [ 50850-93-6 ]
Downstream synthetic route of [ 50850-93-6 ]

[ 50850-93-6 ] Synthesis Path-Upstream 1~1

1
[ 50850-93-6 ]
[ 93-85-6 ]

Reference： [1] Journal of the Chemical Society, 1927, p. 1190
[2] Collection of Czechoslovak Chemical Communications, 1962, vol. 27, p. 1533 - 1548
[3] Patent: US5968942, 1999, A,
[4] Patent: US6046190, 2000, A,

[ 50850-93-6 ] Synthesis Path-Downstream 1~3

1
[ 50850-93-6 ]
[ 99073-88-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 1h;	Step 1: To a solution of tert-butyl nitrite (4.5 mL, 37.5 mmol) and copper(II) bromide (6.0 g, 27 mmol) in CH3CN(100 mL) at rt was added a mixture of ethyl 2-aminobenzo[d]thiazole-6-carboxylate (5.0 g, 22.5 mmol) in CH3CN (50mL). The reaction suspension was stirred at rt for 1 h. The resulting reaction mixture was quenched with 300 mL of 1 NHCl aqueous solution and extracted with CH2Cl2 (3x200 mL). The combined organic layers were dried over MgSO4,and concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture ofCH2Cl2-hexanes (4:1, v/v) as eluent to give ethyl 2-bromobenzo[d]thiazole-6-carboxylate as a white solid (6.2 g, 96%).1H NMR (300 MHz, CDCl3) delta 8.54 (d, J= 1.1 Hz, 1H), 8.16 (dd, J= 1.5, 8.7 Hz, 1H), 8.02 (d, J = 8.7 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 1.43 (t, J= 7.2 Hz, 3H). LCMS (ESI) m/z 288, 286 (M+H)+.
89%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 0.75h;	Add a solution of commercially available ethyl 2- aminobenzothiazole-6-carboxylate (10 g, 45 mmol) in acetonitrile (40 ML) to a solution of copper (II) bromide (12 G, 54 mmol) and tert-butyl nitrite (9 mL, 75 mmol) in acetonitrile (100 mL) at room temperature under nitrogen and stir for 45 min. Dilute the mixture with 1 N HCL (300 mL) and extract with methylene chloride (3 x 300 mL). Wash the combined organic extracts with water (300 mL), dry over MGS04, filter though a plug of silica gel and remove the solvents under reduced pressure to afford ethyl 2- bromobenzothiazole-6-carboxylate (Step 1) as an off-white solid (11.5 g, 89%): 1H NMR (CDC13) 5 1.40 (t, 3H), 4.40 (q, 2H), 8.00 (d, 1H), 8.20 (d, 1H), 8.60 (s, 1H).
		(195-4) Ethyl 2-bromo-1,3-benzothiazole-6-carboxylate was obtained from the compound of Example 195-3 in a similar manner to Example 125-2. 1H NMR (CDCl3, 400 MHz) delta 9.71 (brs, 1H), 9.16 (s, 1H), 8.56 (d, 1H, J=1.2 Hz), 8.24 (d, 1H, J=8.5 Hz), 8.09 (dd, 1H, J=8.5, 1.2 Hz), 7.19 (m, 1H), 6.95 (m, 1H), 6.39 (m, 1H).

		(195-4) Ethyl 2-bromo-1,3-benzothiazole-6-carboxylate was obtained from the compound of Example 195-3 in a similar manner to Example 125-2. 1H NMR (CDCl3, 400MHz) delta 9.71 (brs, 1H), 9.16 (s, 1H), 8.56 (d, 1H, J=1.2Hz), 8.24 (d, 1H, J=8.5Hz), 8.09 (dd, 1H, J=8.5, 1.2Hz), 7.19 (m, 1H), 6.95 (m, 1H), 6.39 (m, 1H).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 2.16667h;Inert atmosphere;	EXAMPLE 1; 2-[l-(3,4,5-Tribromobenzyl)-lH-L2,3-triazol-4-yl]-L3-benzothiazole-6-carboxylic acid Step 1: Ethyl 2-bromo-L3-benzothiazole-6-carboxylateA suspension Of CuBr2 (1.20 g, 5.40 mmol) in anhydrous acetonitrile (15 niL) was purged with nitrogen. The mixture was cooled in an ice-bath and treated with t- BuONO (696 mg, 6.75 mmol). After further stirring for 10 min at about 0 to 5 0C, the mixture was reacted with 2-amino-l,3-benzothiazole-6-carboxylate (1.0 g, 4.5 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h. The mixture was then diluted with water (30 mL) and extracted with ether (100 mL x 2). The combined organic phase was filtered to removed copper salts, then washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated to afford the title compound.1H NMR (CDCl3, 400 MHz): delta 8.54 (d, IH), 8.16 (dd, IH), 8.02 (d, IH), 4.42 (q, 2H), 1.42 (t, 3H).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 2h;	STEP A: Ethyl 2-aminobenzothiazole-6-carboxylate (8.91 g) and CuBr2 (13.43 g) were combined in acetonitrile (300 mL). To the resulting deep green solution was added tert-butylnitrite (7.14 mL). The resulting mixture was heated to ~65 C for two hours, then concentrated to ~50 mL. The resulting concentrate was diluted with water (250 mL) and extracted with EtOAc (2*250 mL). The resulting yellow solution was concentrated to yield ethyl 2-bromobenzo[d]thiazole-6-carboxylate as a yellow solid. 1H NMR delta 8.55 (s, 1H), 8.16 (dd, 1H, J=8.6, 1.7 Hz), 8.03 (d, 1H, J=8.3 Hz), 4.43 (q, 2H, J=7.1 Hz), 1.43 (t, 3H, J=7.1 Hz). MS: 286.0 (M+H).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 14h;Cooling with ice;	To the solution of ethyl 2-aminobenzo[d]thiazole-6-carboxylate (8.0 g, 36.0 mmol) and CuBr2 (16.07 g, 72.0 mmol) in acetonitrile (200 mL), tert-butyl nitrite (7.42 mL, 72.0 mmol) was added on ice bath. The reaction mixture was stirred at room temperature for 14 h. The solvent was removed under reduced pressure and to the residue ethyl acetate (200 mL) and NH4Cl solution (200 mL) were added. The organic phase was washed with brine (100 mL) and NH4Cl solution (100 mL), dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. Yield: 8.0 g (78%); pale brown solid. (0862) 1H NMR (400 MHz, DMSO-d6): d 1.36 (t, J = 7.1 Hz, 3H), 4.37 (q, J = 7.1 Hz, 2H), 8.10 (s, 2H), 8.82 (s, 1H) ppm.

Reference： [1]Patent: EP2766359,2016,B1 .Location in patent: Paragraph 0319
[2]Patent: WO2004/63155,2004,A1 .Location in patent: Page 148-149
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1874 - 1879
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 437
Chem.Abstr.,1958,p. 14589
[5]Patent: US2003/181496,2003,A1
[6]Patent: EP1479384,2004,A1
[7]Patent: WO2010/37225,2010,A1 .Location in patent: Page/Page column 42
[8]Patent: US2011/152287,2011,A1 .Location in patent: Page/Page column 21
[9]Patent: WO2020/48949,2020,A1 .Location in patent: Page/Page column 98

2
[ 50850-93-6 ]
[ 7789-45-9 ]
[ 99073-88-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; In acetonitrile;	Step 2 2-Bromo-6-ethoxycarbonylbenzothiazole A mixture of copper(II) bromide (2.70 g, 12.09 mmol) and anhydrous acetonitrile (50 mL) was purged with nitrogen, cooled in an ice bath, treated with tert-butyl nitrite (1.8 mL, 15.13 mmol), stirred 10 minutes at 0-5 C., and then treated with solid 2-amino-6ethoxycarbonylbenzothiazole (2.24 g, 10.08 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water (300 mL) and extracted with ether (2*100 mL). The extracts were filtered to remove copper salts, then washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and evaporated under vacuum to provide crude 2-bromo-6-ethoxycarbonylbenzothiazole (1.90 g) as an orange-tan solid. 1 H NMR (CDCl3, 500 MHz) delta1.42 (t, CH3), 4.42 (q, CH2), 8.02 (d, H-4), 8.15 (dd, H-5), and 8.53 (d, H-7). 13 C NMR (CDCl3, 125.7 MHz) delta14.3, 61.5, 122.5, 122.9, 127.8, 137.2, 142.3, 155.0, and 156.7.
	With tert.-butylnitrite; In acetonitrile;	Step 2 2-Bromo-6-ethoxycarbonylbenzothiazole A mixture of copper(II) bromide (2.70 g, 12.09 mmol) and anhydrous acetonitrile (50 mL) was purged with nitrogen, cooled in an ice bath, treated with tert-butyl nitrite (1.8 mL, 15.13 mmol), stirred 10 minutes at 0-5 C., and then treated with solid 2-amino-6 -ethoxycarbonylbenzothiazole (2.24 g, 10.08 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water (300 mL) and extracted with diethyl ether (2*100 mL). The extracts were filtered to remove copper salts, then washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and evaporated under vacuum to provide crude 2-bromo-6-ethoxycarbonylbenzothiazole (1.90 g) as an orange-tan solid. 1 H NMR (CDCl3, 500 MHz) delta1.42 (t, CH3), 4.42 (q, CH2), 8.02(d, H-4), 8.15 (dd, H-5), and 8.53 (d, H-7). 13 C NMR (CDCl3, 125.7 MHz) delta14.3, 61.5, 122.5, 122.9, 127.8, 137.2, 142.3, 155.0, and 165.7.
	With tert.-butylnitrite; In acetonitrile;	Step 2 2-Bromo-6-ethoxycarbonylbenzothiazole A mixture of copper(II) bromide (2.70 g, 12.09 mmol) and anhydrous acetonitrile (50 mL) was purged with nitrogen, cooled in an ice bath, treated with tert-butyl nitrite (1.8 mL, 15.13 mmol), stirred 10 minutes at 0-5 C., and then treated with solid 2-amino-6 ethoxycarbonylbenzothiazole (2.24 g, 10.08 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with water (300 mL) and extracted with diethyl ether (2*100 mL). The extracts were filtered to remove copper salts, then washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and evaporated under vacuum to provide crude 2-bromo-6-ethoxycarbonylbenzothiazole (1.90 g) as an orange-tan solid. 1 H NMR (CDCl3, 500 MHz) delta1.42 (t, CH3), 4.42 (q, CH2), 8.02(d, H-4), 8.15 (dd, H-5), and 8.53 (d, H-7). 13 C NMR (CDCl3, 125.7 MHz) delta14.3, 61.5, 122.5, 122.9, 127.8, 137.2, 142.3, 155.0, and 165.7.

Reference： [1]Patent: US5496816,1996,A
[2]Patent: US5498777,1996,A
[3]Patent: US5538964,1996,A

3
[ 50850-93-6 ]
[ 41360-32-1 ]
C₁₈H₁₆N₂O₆S₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9094 - 9106

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Technical Information

? Acyl Group Substitution ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Amines ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

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H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 50850-93-6 ] {[proInfo.proName]}

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[ 50850-93-6 ] Synthesis Path-Upstream 1~1

[ 50850-93-6 ] Synthesis Path-Downstream 1~3

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