[ CAS No. 20358-03-6 ] {[proInfo.proName]}

Name: 20358-03-6|2-Amino-5-bromobenzothiazole|97%
Brand: Ambeed
SKU: A129033
Price: 5.0 USD
Availability: InStock
Rating: 93 (27 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 20358-03-6 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 20358-03-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20358-03-6 ]

SDS Specification

Alternatived Products of [ 20358-03-6 ]

Product Details of [ 20358-03-6 ]

CAS No. :	20358-03-6	MDL No. :	MFCD00577806
Formula :	C₇H₅BrN₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZPUJTWBWSOOMRP-UHFFFAOYSA-N
M.W :	229.10	Pubchem ID :	13775785
Synonyms :

Calculated chemistry of [ 20358-03-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.72
TPSA :	67.15 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	2.72
Log Po/w (WLOGP) :	2.65
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	3.1
Consensus Log Po/w :	2.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.0603 mg/ml ; 0.000263 mol/l
Class :	Soluble
Log S (Ali) :	-3.78
Solubility :	0.0377 mg/ml ; 0.000164 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.47
Solubility :	0.0776 mg/ml ; 0.000339 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 20358-03-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20358-03-6 ]

* 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 [ 20358-03-6 ]
Downstream synthetic route of [ 20358-03-6 ]

[ 20358-03-6 ] Synthesis Path-Upstream 1~10

1
[ 20358-03-6 ]
[ 583-53-9 ]
[ 66820-95-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 9, p. 1420 - 1422[2] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 9, p. 1521 - 1524,3

2
[ 21327-14-0 ]
[ 20358-03-6 ]

Reference： [1] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[2] Patent: US2004/44258, 2004, A1, . Location in patent: Page 97
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1323 - 1331
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824

3
[ 1147550-11-5 ]
[ 591-19-5 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: at 20℃; for 1.5 h; Stage #2: at 0 - 20℃; for 1 h;	General procedure: To a solution of the commercially available aniline (1.0 eq) in acetic acid (0.5 M), was added ammonium thiocyanate (5.0 eq) at rt. After 90 min, the thick suspension was cooled to 0°C, and bromine (1.1 eq) in acetic acid (1.0 M) was added. After 1 h, the reaction was allowed to warm to rt. After a subsequent 1 h, the mixture wasconcentrated to remove acetic acid. A small amount of water was added, then the mixture was adjusted to pH 12 with concentrated ammonium hydroxide. The resulting mixture was extracted with EtOAc (x3) and the combined organics were washed withNaHC03(_Sat), brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography and/or recrystallization from EtOAc/Hex to yield the appropriate 2-aminobenzothiazole.

Reference： [1] Patent: WO2017/75694, 2017, A1, . Location in patent: Page/Page column 224
[2] Archiv der Pharmazie, 2016, p. 651 - 661

4
[ 854890-84-9 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydride In 1-methyl-pyrrolidin-2-one at 20 - 160℃; for 1 h;	To a solution of 2,5-dibromo-phenyl)-thiourea III (2.0 g, 6.5 mmol) in N- methylpyrrolidone (10 mL) was added NaH (60percent dispersion in mineral oil, 0.24 g, 9.70 mmol) at room temperature. The reaction mixture was heated up to 160⁰C for 1h. After completion of reaction (TLC monitoring), the reaction mixture was allowed to come to room temperature. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate (3x 50 mL). The combined organic layers were dried over anhydrous Na₂SO₄, filtered and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (100 -200M) using hexane and ethyl acetate (80:20) to obtain the desired product as white solid (0.23 g, 16percent). ¹H NMR (DMSO-d6, 400 MHz): δ 7.15 (dd, J= 2.0 and 8.40 Hz, 1 H), 7.47 (d, J= 2.0 Hz, 1 H)₁ 7.62 (d, J= 8.40 Hz, 1 H) and 7.68 (br s, 2H). MS: 229.01 (M+H⁺).

Reference： [1] Patent: WO2009/74812, 2009, A1, . Location in patent: Page/Page column 16; 17

5
[ 21327-14-0 ]
[ 20358-03-6 ]
[ 20358-05-8 ]

Reference： [1] Patent: WO2013/43001, 2013, A1, . Location in patent: Paragraph 838; 839
[2] Patent: US2015/11528, 2015, A1, . Location in patent: Paragraph 0484

6
[ 56967-17-0 ]
[ 20358-03-6 ]

Reference： [1] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148

7
[ 591-19-5 ]
[ 20358-03-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824

8
[ 333-20-0 ]
[ 591-19-5 ]
[ 20358-03-6 ]

Reference： [1] Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 3969 - 3974

9
[ 157645-54-0 ]
[ 20358-03-6 ]

Reference： [1] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272

10
[ 875-51-4 ]
[ 20358-03-6 ]

Reference： [1] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272

[ 20358-03-6 ] Synthesis Path-Downstream 1~88

1
[ 157645-54-0 ]
[ 20358-03-6 ]

Reference： [1]Journal of the Chemical Society C: Organic,1969,p. 268 - 272

2
[ 4394-85-8 ]
[ 20358-03-6 ]
[ 112446-68-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1987,vol. 52,p. 1006 - 1014

3
[ 20358-03-6 ]
[ 98-09-9 ]
N-(5-Bromo-benzothiazol-2-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 311 - 318

4
[ 20358-03-6 ]
[ 98-09-9 ]
[ 103-70-8 ]
N-(5-Bromo-benzothiazol-2-yl)-benzenesulfonamide [ No CAS ]
N-[5-Bromo-3-[(E)-phenyliminomethyl]-3H-benzothiazol-(2Z)-ylidene]-benzenesulfonamide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 311 - 318

5
[ 20358-03-6 ]
1<i>H</i>-benzoimidazole-2-carboxylic acid (5-bromo-benzothiazol-2-yl)-amide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 1289 - 1294

6
[ 875-51-4 ]
[ 20358-03-6 ]

Reference： [1]Journal of the Chemical Society C: Organic,1969,p. 268 - 272

7
[ 21327-14-0 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In chloroform; at 20℃; for 18.5h;Heating / reflux;	Synthesis of 2-amino-5-bromobenzothiazole (Intermediate 63) A solution of Intermediate 62 (1.29 g) in chloroform (12 ml) was added dropwise with a solution of bromine (272 mul, WAKO) in chloroform (1.5 ml), refluxed with heating for 2.5 hours and then stirred at room temperature for 16 hours.The reaction mixture was concentrated under reduced pressure, neutralized with 5percent aqueous ammonia and then added with water (50 ml) and methylene chloride (150 ml) for extraction.The organic layer was dried, and then the solvent was evaporated under reduced pressure.The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 63, 609 mg).

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148
[2]Patent: US2004/44258,2004,A1 .Location in patent: Page 97
[3]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 9814 - 9824

8
[ 20358-03-6 ]
[ 5419-55-6 ]
[ 590417-69-9 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of methyl 3-[3-(2-aminobenzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]Propionate (Compound No. 284) (Preparation Method 4, Step d-1) A solution of Intermediate 63 (459.1 mg) in anhydrous THF (30 ml) was added with N,N,N',N'-tetramethylethylenediamine (1.51 ml, WAKO), cooled to -78° C. under argon atmosphere, then added dropwise with 1.62 M solution of t-butyllithium in pentane (7.06 ml) and stirred for 30 minutes.The reaction mixture was added dropwise with (iPrO)3B (2.77 ml), stirred for 30 minutes, then warmed to room temperature and further stirred for 1.5 hours.The reaction mixture was added with 0.5 M aqueous sulfuric acid (7.5 ML) and extracted with diethyl ether (50 ml*3).The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 2-amino-5-benzothiazoleboronic acid.According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 12 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1), the above compound was reacted with Intermediate 3 (344 mg), 2 M aqueous sodium carbonate (4.5 ml) and (Ph3P)4Pd (179 mg) and treated to obtain the title compound (Compound No. 284, 76 mg).

Reference： [1]Patent: US2004/44258,2004,A1 .Location in patent: Page 97-98

9
[ 20358-03-6 ]
[ 109-90-0 ]
[ 1160789-85-4 ]

Yield	Reaction Conditions	Operation in experiment
50 - 60%	In 1,4-dioxane; at 78 - 80℃; for 16h;Product distribution / selectivity;	To a suspension of 5-bromo-benzothiazol-2-ylamine IV (0.23 g, 1.0 mmol) in 1, 4- dioxane (10 mL) was added ethylisocyanate (0.36 g, 0.38 mL, 5.02 mmol). The reaction mixture was heated up to 78-8O0C overnight. After completion of reaction (TLC monitoring), 1 , 4-dioxane was distilled off and co evaporated with hexane. The resulting solid was treated with water to 60-700C for 3-5 h. The resulting solid was <n="19"/>filtered off and again washed with hot water, dried under high vacuum to obtain the desired product as off-white solid (0.15 g, 50percent). 1H NMR (DMSO-d6, 400 MHz): delta 1.08 (t, J= 7.20 Hz, 3H), 3.18 (m, 2H), 6.70 (br s, 1H), 7.36 (dd, J= 1.60 and 8.0 Hz, 1 H), 7.79 (d, J = 1.60 Hz1 1 H), 7.84 (d, J= 8.40 Hz, 1 H) and 10.85 (br s, 1 H). MS: 300.07 (M+H+).; To a solution of 2-amino-5-bromo benzothiazole (0.23 g, 1.0 mmol) in 1 ,4-dioxane (8.0 mL) was added ethylisocyanate (3.96 ml_, 5.0 mmol) and the resulting solution was heated to 8O0C for 16 h. After the completion of the reaction (TLC monitoring), 1 ,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 9O0C for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (0.18 g, 60percent).

Reference： [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 16; 17-18; 22

10
[ 854890-84-9 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydride; In 1-methyl-pyrrolidin-2-one; at 20 - 160℃; for 1h;	To a solution of 2,5-dibromo-phenyl)-thiourea III (2.0 g, 6.5 mmol) in N- methylpyrrolidone (10 mL) was added NaH (60percent dispersion in mineral oil, 0.24 g, 9.70 mmol) at room temperature. The reaction mixture was heated up to 1600C for 1h. After completion of reaction (TLC monitoring), the reaction mixture was allowed to come to room temperature. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate (3x 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (100 -200M) using hexane and ethyl acetate (80:20) to obtain the desired product as white solid (0.23 g, 16percent). 1H NMR (DMSO-d6, 400 MHz): delta 7.15 (dd, J= 2.0 and 8.40 Hz, 1 H), 7.47 (d, J= 2.0 Hz, 1 H)1 7.62 (d, J= 8.40 Hz, 1 H) and 7.68 (br s, 2H). MS: 229.01 (M+H+).

Reference： [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 16; 17

11
[ 45891-21-2 ]
[ 20358-03-6 ]
[ 1223564-61-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

12
[ 20358-03-6 ]
[ 41834-87-1 ]
1-butyryl-3-(5-bromobenzo[d]thiazol-2-yl) thiourea [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

13
[ 20358-03-6 ]
[ 68967-37-3 ]
[ 1223564-47-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

14
[ 20358-03-6 ]
[ 532-55-8 ]
[ 1223564-51-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

15
[ 20358-03-6 ]
[ 28115-92-6 ]
[ 1223564-43-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331

16
C₁₄H₁₀BrN₂OPolS [ No CAS ]
[ 20358-03-6 ]
[ 20358-05-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 644 - 648

17
C₁₄H₈BrN₂OPolS [ No CAS ]
[ 20358-03-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 644 - 648

18
[ 20358-03-6 ]
[ 23451-95-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2777 - 2784

19
[ 20358-03-6 ]
2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(5-bromobenzo[d]thiazol-2-yl)acetamide [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2011,vol. 23,p. 3969 - 3974

20
[ 333-20-0 ]
[ 591-19-5 ]
[ 20358-03-6 ]

Reference： [1]Asian Journal of Chemistry,2011,vol. 23,p. 3969 - 3974

21
[ 20358-03-6 ]
2-amino-5-[(E)-phenyldiazenyl]benzoyl chloride [ No CAS ]
C₂₀H₁₄BrN₅OS [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

22
[ 20358-03-6 ]
C₂₇H₁₆BrN₅OS [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

23
[ 20358-03-6 ]
[ 1309261-76-4 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

24
[ 20358-03-6 ]
[ 1309261-61-7 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

25
[ 20358-03-6 ]
[ 1022-46-4 ]
[ 1309261-61-7 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

26
[ 56967-17-0 ]
[ 20358-03-6 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148

27
[ 20358-03-6 ]
[ 4334-87-6 ]
[ 1415695-82-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7719 - 7725

28
[ 20358-03-6 ]
[ 179113-90-7 ]
[ 1415695-83-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7719 - 7725

29
[ 20358-03-6 ]
[ 583-53-9 ]
[ 66820-95-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2012,vol. 48,p. 1420 - 1422
Khim. Geterotsikl. Soedin.,2012,vol. 48,p. 1521 - 1524,3

30
[ 21327-14-0 ]
[ 20358-03-6 ]
[ 20358-05-8 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In dichloromethane; at 20℃;	[838] Step 1: a mixture of 5-bromobenzo[d]thiazol-2-amine and 7-bromobenzo[d]thiazol-2-amine[839] To a stirred solution of 1-(3-bromophenyl)thiourea (1.00 g, 4.33 mmol) in dichloromethane (15 mL) was added dropwise a solution of bromine (345 mg, 4.33 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature overnight. The resulting solid was filtered, washed with dichloromethane, and then dried under reduced pressure to give 809 mg of the titled compound as a yellow solid (Yield: 82percent).
	With bromine; In dichloromethane; at 20℃;	Step 1: a mixture of 5-bromobenzo[d]thiazol-2-amine and 7-bromobenzo[d]thiazol-2-amine [0484] To a stirred solution of 1-(3-bromophenyl)thiourea (1.00 g, 4.33 mmol) in dichloromethane (15 mL) was added dropwise a solution of bromine (345 mg, 4.33 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature overnight. The resulting solid was filtered, washed with dichloromethane, and then dried under reduced pressure to give 809 mg of the titled compound as a yellow solid (Yield: 82percent).

Reference： [1]Patent: WO2013/43001,2013,A1 .Location in patent: Paragraph 838; 839
[2]Patent: US2015/11528,2015,A1 .Location in patent: Paragraph 0484

31
[ 20358-03-6 ]
(5-bromo-benzothiazol-2-yl)-hydrazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5514 - 5540

32
[ 20358-03-6 ]
[ 1135869-10-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5514 - 5540

33
[ 20358-03-6 ]
[ 625-95-6 ]
[ 1453813-81-4 ]