Home Cart 0 Sign in  

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

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 50850-93-6
Chemical Structure| 50850-93-6
Structure of 50850-93-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 50850-93-6 ]

Related Doc. of [ 50850-93-6 ]

Alternatived Products of [ 50850-93-6 ]
Product Citations

Product Details of [ 50850-93-6 ]

CAS No. :50850-93-6 MDL No. :MFCD00102724
Formula : C10H10N2O2S Boiling Point : -
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 Ų

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: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 [ 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   1~18

  • 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,
  • 2
  • [ 333-20-0 ]
  • [ 94-09-7 ]
  • [ 50850-93-6 ]
YieldReaction ConditionsOperation in experiment
100% at 19 - 20℃; Ethyl 4-aminobenzoate (4.9 g, 30.0 mmol) and potassium thiocyanate (11.6 g,120.0 mmol) are dissolved in acetic acid(180 mL), followed by dripping acetic acid solution(20 mL) with bromine (1.5 mL,30.0 mmol) at 19 °C in 20 min, then the temperature is increased to room temperature and the mixture continues to react overnight.
Then, the reaction solution is poured into water (100 mL), and stirred for 10 min, then ammonium hydroxide is dripped into the mixture to regulate pH to approximately 8, then the mixture is filtered, wherein filter cake is successively washed with water and petroleum ether, and finally the product is vacuumed to dryness, so as to obtain a yellow solid of 6.7 g, that is ethyl 2-aminobenzo[d]thiazole-6-carboxylate, with a yield of 100percent.
Spectrum is: 1H NMR (400 MHz, DMSO) δ: 8.28(d, J = 1.6 Hz, 1H), 7.88(s ,2H), 7.82(dd, J = 1.6 Hz, 8.4 Hz, 1H), 7.37(d, J = 8.4Hz, 1H), 4.29(q, J = 7.2 Hz ,2H), 1.32(t, J = 7.2 Hz, 3H).
97% With copper(ll) sulfate pentahydrate In methanol for 6 h; Reflux To methanol (800 mL) were added ethyl 4-aminobenzoate 4 (49.5 g, 0.3 mol), KSCN (291 g, 3 mol) and CuSO4*5H2O (275 g,1.5 mol). The mixture was heated to reflux by mechanical stir for 6 h. After cooling to room temperature, the precipitate was filtered, about 2/3 of the filtrate was evaporated under reduced pressure. Water (600 mL) was added, the precipitate obtained was filtered and added to 2 N NaOH solution (500 mL), stirred for 10 min at room temperature. The precipitate was filtered, washed with waterand dried to get 5 (52.6 g, 79percent) as white powder, mp: 242-243 °C([45], mp, 241-242 °C).
69%
Stage #1: at 20℃; for 0.333333 h;
Stage #2: at 10 - 20℃;
Ethyl 4-aminobenzoate (1 eq.) and KSCN (4 eq.) were dissolved in acetic acid (4 mL/mmol) and stirred at rt for 20mins. Then the reaction mixture was cooled to 10 °C and bromine (2 eq.) dissolved in small amount of acetic acid was added dropwise. Afterwards the reaction mixture was left to warm up to rt and stirred overnight. After the reaction was completed (monitored by TLC), reaction mixture was added dropwise into the sat. aq. NH3 solution (15 mL/mmol) while cooling in an ice bath. The product was extracted to EtOAc and the organic layer was washed with Na2S2O3, sat. aq. NaHCO3 and brine, dried using anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was recrystallized from diethyl ether to obtain ethyl 2-aminobenzo[d]thiazole-6-carboxylate in 69percent yield. 1H NMR (500 MHz, DMSO-d6): (ppm) 8.27 (d, J = 1.8Hz, 1H), 7.88 (s, 2H), 7.81 (dd, J = 8.4, 1.8 Hz, 1H), 7.36 (d,J = 8.4 Hz, 1H), 4.27 (q, J = 7.1 Hz, 2H), 1.30 (t, J = 7.1 Hz,3H).
67%
Stage #1: at 20℃;
Stage #2: With ammonium hydroxide In water
Compound 28 (2.0 g, 12 mmol) was dissolved in 16 mL of acetic acid, and to the resulting solution was suspended potassium thiocyanate (4.67 g, 48 mmol). A solution of 0.61 mL of bromine in 8 ml of acetic acid was slowly added, and the reaction mixture was stirred at room temperature overnight. Water was added and the mixture was made neutral by addition of aqueous ammonium hydroxide. The precipitation was collected by filtration and then washed with water and subsequently dried to afford compound 29 (1.80 g, 67percent) as light yellow solid. The compound was used, without structure determination, directly for the next step.
50% With copper(II) sulfate In methanol at 70℃; for 5 h; Step: 1 Preparation of ethyl 2-amino-l,3-benzothiazole-6-carboxylate.A mixture of ethyl-4-amino benzoate (1.65g, lOmmol), KCNS (9.72g, 100 mmol) and CuSO4 (8g, 50mmol) in methanol (3OmL) was stirred for 5 hours at 7O0C. Subsequently, the suspension was cooled and filtered; the filtrate was diluted with water (4OmL) and heated to boiling. Ethanol was added to the boiling filtrate until a clear, although slightly yellowish solution was formed. Cooling of this solution resulted in crystallization of the product (l.lg, 50percent yield) as a pale yellow solid. NMR <n="17"/>o(DMSO-de) 1H δ (ppm): 8.34 (IH, d, Ar-H), 7.87 (IH, dd, Ar-H), 7.42 (IH, d, Ar-H), 4.30 (2H, q, CH2), and 1.32 (3H, t, CH3). MS m/z: 223 (M+l)
46% at 10 - 20℃; [1067] Step 1: ethyl 2-aminobenzo[d]thiazol-6-carboxylate[1068] To a solution of ethyl 4-aminobenzoate (16.5 g, 100.0 mmol) and potassium thiocyanate (10.7 g, 110.0 mmol) in acetic acid (150 mL) was added dropwise a solution of bromine (5.1 mL, 100.0 mmol) in acetic acid (50 mL) at below 10 ℃. The reaction mixture was stirred at room temperature overnight. The resulting solid was filtered and then dissolved in warm water (50 ℃). The aqueous layer was washed with chloroform and then basified to pH 11 with solid sodium carbonate. The resulting solid was filtered, washed with water, and then dried under reduced pressure to give 10.2 g of the titled compound as a white solid (Yield: 46percent).
46% at 10 - 20℃; Step 1:
ethyl 4-aminobenzo[d]thiazol-6-carboxylate
To a solution of ethyl 4-aminobenzoate (16.5 g, 100.0 mmol) and potassium thiocyanate (10.7 g, 110.0 mmol) in acetic acid (150 mL) was added dropwise a solution of bromine (5.1 mL, 100.0 mmol) in acetic acid (50 mL) at below 10° C.
The reaction mixture was stirred at room temperature overnight.
The resulting solid was filtered and then dissolved in warm water (50° C.).
The aqueous layer was washed with chloroform and then basified to pH 11 with solid sodium carbonate.
The resulting solid was filtered, washed with water, and then dried under reduced pressure to give 10.2 g of the titled compound as a white solid (Yield: 46percent).

Reference: [1] Patent: EP3401315, 2018, A1, . Location in patent: Paragraph 0062; 0063
[2] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[3] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 702 - 712
[4] Medicinal Chemistry, 2017, vol. 13, # 4, p. 345 - 358
[5] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498
[7] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2509 - 2522
[8] Patent: WO2007/113644, 2007, A2, . Location in patent: Page/Page column 15-16
[9] Patent: WO2013/43001, 2013, A1, . Location in patent: Paragraph 1067; 1068
[10] Patent: US2015/11528, 2015, A1, . Location in patent: Paragraph 0600
[11] Journal of Medicinal Chemistry, 1999, vol. 42, # 15, p. 2828 - 2843
[12] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565
  • 3
  • [ 94-09-7 ]
  • [ 50850-93-6 ]
YieldReaction ConditionsOperation in experiment
31% With bromine In acetic acid (195-1)
A solution of ethyl p-aminobenzoate (23.2 g) and potassium thiocyanate (40.9 g) in acetic acid (280 mL) was cooled to 0° C., and thereto was added dropwise bromine (22.4 g), and the mixture was stirred at 0° C. for 20 minuts, and stirred at room temperature for 135 minutes, and stirred for 5 hours.
The precipitated solid was collected by filtration to give ethyl 2-amino-1,3-benzothiazole-6-carboxylate (9.62 g, 31percent)
1H NMR (DMSO-d6, 400 MHz) δ 8.65 (brs, 2H), 8.38 (d, 1H, J=1.7 Hz), 7.89 (dd, 1H, J=8.5, 1.7 Hz), 7.44 (d, 1H, J=8.5 Hz), 4.30 (q, 2H, J=7.1 Hz), 1.32 (t, 3H, J=7.1 Hz).
31% With bromine In acetic acid (195-1)
A solution of ethyl p-aminobenzoate (23.2 g) and potassium thiocyanate (40.9 g) in acetic acid (280 mL) was cooled to 0°C, and thereto was added dropwise bromine (22.4 g), and the mixture was stirred at 0°C for 20 minuts, and stirred at room temperature for 135 minutes, and stirred for 5 hours.
The precipitated solid was collected by filtration to give ethyl 2-amino-1,3-benzothiazole-6-carboxylate (9.62 g, 31 percent).
1H NMR (DMSO-d6, 400MHz) δ 8.65 (brs, 2H), 8.38 (d, 1H, J=1.7Hz), 7.89 (dd, 1H, J=8.5, 1.7Hz), 7.44 (d, 1H, J=8.5Hz), 4.30 (q, 2H, J=7.1Hz), 1.32 (t, 3H, J=7.1Hz).
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
[3] Patent: US5496816, 1996, A,
[4] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 215[5] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 205
[6] Patent: US5498777, 1996, A,
[7] Patent: US5538964, 1996, A,
  • 4
  • [ 17159-79-4 ]
  • [ 17356-08-0 ]
  • [ 50850-93-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 11, p. 2604 - 2607
  • 5
  • [ 540-72-7 ]
  • [ 94-09-7 ]
  • [ 50850-93-6 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1962, vol. 27, p. 1533 - 1548
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 1, p. 105 - 111
[3] Tetrahedron, 2005, vol. 61, # 38, p. 9075 - 9081
  • 6
  • [ 1147550-11-5 ]
  • [ 94-09-7 ]
  • [ 50850-93-6 ]
Reference: [1] Farmaco, 1994, vol. 49, # 3, p. 153 - 166
[2] Yakugaku Zasshi, 1950, vol. 70, p. 271,276[3] Chem.Abstr., 1951, p. 10212
  • 7
  • [ 114224-05-4 ]
  • [ 50850-93-6 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 215[2] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 205
[3] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 215[4] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 205
[5] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 215[6] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 205
[7] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 215[8] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 205
  • 8
  • [ 23933-10-0 ]
  • [ 50850-93-6 ]
Reference: [1] Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1969, vol. 302, # 7, p. 511 - 517
  • 9
  • [ 150-13-0 ]
  • [ 50850-93-6 ]
Reference: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
[3] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
  • 10
  • [ 93-85-6 ]
  • [ 50850-93-6 ]
Reference: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
  • 11
  • [ 23051-16-3 ]
  • [ 50850-93-6 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 1190
  • 12
  • [ 15192-76-4 ]
  • [ 94-09-7 ]
  • [ 50850-93-6 ]
Reference: [1] Chemische Berichte, 1934, vol. 67, p. 944,947
[2] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[3] Chem.Abstr., 1952, p. 112
  • 13
  • [ 2536-91-6 ]
  • [ 50850-93-6 ]
Reference: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
  • 14
  • [ 20600-51-5 ]
  • [ 50850-93-6 ]
Reference: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
  • 15
  • [ 50850-93-6 ]
  • [ 99073-88-8 ]
YieldReaction ConditionsOperation in experiment
96% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃; for 1 h; 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, 96percent).1H NMR (300 MHz, CDCl3) δ 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 0.75 h; 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, 89percent): 1H NMR (CDC13) 5 1.40 (t, 3H), 4.40 (q, 2H), 8.00 (d, 1H), 8.20 (d, 1H), 8.60 (s, 1H).
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, # 6, p. 1874 - 1879
[4] Yakugaku Zasshi, 1958, vol. 78, p. 437[5] Chem.Abstr., 1958, p. 14589
[6] Patent: US2003/181496, 2003, A1,
[7] Patent: EP1479384, 2004, A1,
[8] Patent: WO2010/37225, 2010, A1, . Location in patent: Page/Page column 42
[9] Patent: US2011/152287, 2011, A1, . Location in patent: Page/Page column 21
  • 16
  • [ 50850-93-6 ]
  • [ 7789-45-9 ]
  • [ 99073-88-8 ]
Reference: [1] Patent: US5496816, 1996, A,
[2] Patent: US5498777, 1996, A,
[3] Patent: US5538964, 1996, A,
  • 17
  • [ 50850-93-6 ]
  • [ 114224-05-4 ]
  • [ 2268-79-3 ]
Reference: [1] Patent: US5538964, 1996, A,
  • 18
  • [ 50850-93-6 ]
  • [ 78485-37-7 ]
YieldReaction ConditionsOperation in experiment
86% With tert.-butylnitrite; copper dichloride In acetonitrile at 0 - 20℃; Cupric chloride (6.0 g, 44.6 mmol), tert-butyl nitrite (7.1 mL, 59.4 mmol) and acetonitrile (200 mL) are added to a 500 ml single neck bottle and the mixture is cooled to 0 °C, followed by adding ethyl 2-aminobenzo[d]thiazole-6-carboxylate (6.6 g, 29.7 mmol) in batches in 30 min, then the temperature is increased to room temperate, the mixture reacts overnight, then it is filtered with siliceousearth, and 1HCL (60 mL) is dripped into the filtrate, and the mixture is stirred for 10min, and forms layering, wherein the aqueous layer is extracted with ethyl acetate (100 mL), and the organic layer is combined, washed with saturated salt solution, dried with anhydrous Na2SO4, then filtered again, rotated to dryness and purified by column chromatography (PE:EA= 25:1), so as to obtain a light yellow of 6.2 g, that is ethyl 2-chlorobenzo[d]thiazole-6-carboxylate, with a yield of 86percent.
Spectrum is: 1H NMR (400 MHz, CDCl3) δ: 8.54(d, J = 0.8 Hz, 1H), 8.20(dd, J = 1.6 Hz, 8.4 Hz, 1H), 8.01(d, J = 8.0Hz, 1H), 4.45(q, J = 7.2 Hz, 2H), 1.45(t, J = 7.2 Hz, 3H).
Reference: [1] Patent: EP3401315, 2018, A1, . Location in patent: Paragraph 0062; 0064
[2] Farmaco, 1994, vol. 49, # 3, p. 153 - 166
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 50850-93-6 ]

Esters

Chemical Structure| 436088-66-3

[ 436088-66-3 ]

2-Methoxyethyl 2-aminobenzo[d]thiazole-6-carboxylate

Similarity: 0.99

Chemical Structure| 209459-11-0

[ 209459-11-0 ]

Methyl 2-aminobenzo[d]thiazole-7-carboxylate

Similarity: 0.92

Chemical Structure| 73931-63-2

[ 73931-63-2 ]

Methyl benzo[d]thiazole-6-carboxylate

Similarity: 0.87

Chemical Structure| 677304-89-1

[ 677304-89-1 ]

Ethyl 2-aminobenzo[d]thiazole-7-carboxylate

Similarity: 0.87

Chemical Structure| 66947-92-0

[ 66947-92-0 ]

Methyl 2-amino-1,3-benzothiazole-6-carboxylate

Similarity: 0.87

Amines

Chemical Structure| 436088-66-3

[ 436088-66-3 ]

2-Methoxyethyl 2-aminobenzo[d]thiazole-6-carboxylate

Similarity: 0.99

Chemical Structure| 93-85-6

[ 93-85-6 ]

2-Aminobenzo[d]thiazole-6-carboxylic acid

Similarity: 0.94

Chemical Structure| 209459-11-0

[ 209459-11-0 ]

Methyl 2-aminobenzo[d]thiazole-7-carboxylate

Similarity: 0.92

Chemical Structure| 71224-95-8

[ 71224-95-8 ]

2-Aminobenzo[d]thiazole-7-carboxylic acid

Similarity: 0.88

Chemical Structure| 677304-89-1

[ 677304-89-1 ]

Ethyl 2-aminobenzo[d]thiazole-7-carboxylate

Similarity: 0.87