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Chemical Structure| 7210-76-6
Chemical Structure| 7210-76-6
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Product Details of [ 7210-76-6 ]

CAS No. :7210-76-6 MDL No. :MFCD00123414
Formula : C7H10N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :WZHUPCREDVWLKC-UHFFFAOYSA-N
M.W : 186.23 Pubchem ID :343747
Synonyms :
EMTC;NSC 400231

Calculated chemistry of [ 7210-76-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.57
TPSA : 93.45 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 0.19
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.52 mg/ml ; 0.00817 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.137 mg/ml ; 0.000737 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.8
Solubility : 2.92 mg/ml ; 0.0157 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.58

Safety of [ 7210-76-6 ]

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 [ 7210-76-6 ]

* 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 [ 7210-76-6 ]
  • Downstream synthetic route of [ 7210-76-6 ]

[ 7210-76-6 ] Synthesis Path-Upstream   1~26

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Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 5221,5224
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  • [ 20582-55-2 ]
YieldReaction ConditionsOperation in experiment
56% With hypophosphorous acid; sodium nitrite In water at -5 - 20℃; for 3 h; Compound 3a (4.0 g, 21.5 mmol) was dissolved in 106 ml of 30percent H3PO2.Cool to -5 ° C,NaNO2 (3.0 g, 2.0 eq) was dissolved in 12 ml of water.Add dropwise to the reaction solution,After the addition is completed,Transfer to 0 ° C for 1 h, stir at room temperature for 2 h,Cold NaOH (17g, dissolved in 200ml water) is slowly added dropwise.Saturated NaHCO3 solution is neutral,Extracted with Et2O (50mlx3),Column chromatography (PE: EA=50:1v/v),A yellow semisolid 3b (2.1 g, 56percent) was obtained.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6231 - 6235
[2] Patent: CN101921268, 2016, B, . Location in patent: Paragraph 0128; 0131; 0136-0139
[3] Tetrahedron, 2013, vol. 69, # 22, p. 4436 - 4444
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YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In ethanol at 20℃; for 26 h; To a solution of ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate 5 (3.00g, 16.1mmol) in ethanol (100mL) was added 1M sodium hydroxide solution (50.0mL) at room temperature, and the mixture was stirred for 26h. After the volatiles of the mixture were removed in vacuo, water and acetic acid were added to the residue to adjust the pH to 5.0. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to yield 6 (2.48g, 97percent) as a colorless powder. 1H NMR (200MHz, DMSO-d6) δ 2.35 (s, 3H), 7.57 (s, 2H); MS (ESI): m/z 159 [M+H]+, 157 [M−H].
94%
Stage #1: With sodium hydroxide; water In tetrahydrofuranHeating / reflux
Stage #2: With hydrogenchloride In water
A. A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.5 mmol) and NaOH (5.40 g, 135.0 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed in vacuo, and the residue was neutralized with 5percent hydrochloric acid solution to pH 5~6. The precipitate obtained was collected by filtration and dried to afford the crude 2-amino-4-methylthiazole-5- carboxylic acid (5.20 g, 94percent): 1H NMR (300 MHz, DMSO-J6) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) m/z 159.1 (M + 1).
94%
Stage #1: With sodium hydroxide; water In tetrahydrofuran for 18 h; Heating / reflux
PREPARATION 1; Preparation of 2-amino-7V-benzyl-4-methylthiazole-5-carboxamide; A. A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.5 mmol) and NaOH (5.40 g, 135 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed in vacuo, and the residue was <n="93"/>neutralized with 5percent hydrochloric acid solution to pH 5-6. The precipitate obtained was collected by filtration and dried to afford the crude 2-amino-4-methylthiazole-5- carboxylic acid (5.20 g, 94percent): 1H NMR (300 MHz, DMSO-J6) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) nv'z 159.1 (M + 1).; PREPARATION 13; Preparation of 2-amino-4-methyl-7V-(pyridin-3-ylmethyl)thiazole-5-carboxamide; A. A solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.00 mmol) and sodium hydroxide (5.40 g, 135.00 mmol) in the mixture of tetrahydrofuran (60 mL) and water (30 mL) was heated at reflux for 18 hours. The tetrahydrofuran was removed in vacuo, and the aqueous solution was neutralized with 5percent HCl solution to pH 5-6. The precipitated solid was collected by filtration, washed with water and dried to afford 2-amino-4-methylthiazole-5-carboxylic acid as a white solid in 94percent yield (5.20 g): 1H NMR (300 MHz, DMSO-4) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) m'z 159.1 (M + 1 ).
81% With sodium hydroxide In ethanol at 20℃; The thiazole ethyl ester (1.0 g, 5.81 mmol) was treated with 0.5 M ethanolic sodium hydroxide solution (60 mL), overnight at room temperature. The reaction mixture was then cooled in an ice bath, and neutralized with acetic acid. The precipitated acid 2 was filtered, washed with diethyl ether, and dried overnight at 60 °C.Yield: 81percent; off-white crystals, mp 225-227 C (lit. [31] 223 °C). 1HNMR (400 MHz, DMSO-d6): 2.35 (s, 3H, CH3), 7.61 (s, 2H, NH2),12.26(br s, 1H, COOH) ppm. HRMS (ESI): m/z [M H] calcd forC5H7N2O2S 159.1698; found 159.1663.
79% With sodium hydroxide In methanolReflux Ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate(2) (0.075 M) and sodium hydroxide (0.3 M) in methanol were taken in 50 mL round bottom flask. The solution was refluxed with stirring until the reaction was complete. The clear solution was cooled and neutralized with glacial acetic acid and stirred for 30 min. Precipitate obtained was filtered, washed with water, dried and recrystallized with ethanol. The progress of the reaction and purity of the compound were checked by TLC, using benzene : acetone (8 : 2) as mobile phase. Yield: 79percent; m.p.: 160-162°C; IR (KBr v max) : 3370, 3055, 1741, 1645, 1492, 1388, 913, 728 cm-1; 1H-NMR (300 MHz, DMSO-d6, δ, ppm): 2.71 (s, 3H, CH3), 5.98 (bs, 2H, D2O exchangeable NH2), 10.71 (bs, 1H, COOH); 13C-NMR (75 MHz, CDCl3, δ, ppm): 13.91, (CH3), 133.59, 147.27, 169.54 (-C=O), 173.49 (-C-NH2, thiazole); ESI-MS: m/z 159.13 (M+H), 181.17 (M+Na); Analysis: calcd. for C5H6N2O2S: C, 37.97; H, 3.82; N, 17.71percent; found: 37.93; H, 3.84; N, 17.76percent.
75%
Stage #1: With sodium hydroxide; water In tetrahydrofuran for 18 h; Heating / reflux
A. To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (2.19 g, 11.8 mmol) in a 1 :1 mixture of tetrahydrofuran (20 mL) and water (10 mL) was added sodium hydroxide (1.80 g, 45.0 mmol). The reaction mixture was refluxed for 18 hours and allowed to cool down to ambient temperature. The organic solvent was removed in vacuo. The aqueous solution was acidified with 10percent aqueous hydrochloric acid solution. The colorless solid was collected and dried to afford 2-amino-4-methylthiazole-5- carboxylic acid (1.40 g, 75percent): 1H NMR (300 MHz, DMSO-J6) δ 11.95 (s, IH), 7.26 (s, 2H), 2.01 (s, 3H); MS (ES+) m/z 159.3 (M + 1).A. A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.50 mmol) and NaOH (5.40 g, 135.0 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed in vacuo, and the residue was neutralized with 5percent hydrochloric acid solution to pH 5~6. The precipitate obtained was collected by filtration and dried to afford the crude 2-amino-4-methylthiazole-5- carboxylic acid (5.20 g, 94percent): 1H NMR (300 MHz, DMSO-J6) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) m/z 159.1 (M + 1).

Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7578 - 7583
[2] Patent: WO2008/36715, 2008, A1, . Location in patent: Page/Page column 46
[3] Patent: WO2008/127349, 2008, A2, . Location in patent: Page/Page column 91-92; 100
[4] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 728 - 737
[5] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 208 - 220
[6] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1102 - 1107
[7] Acta Poloniae Pharmaceutica - Drug Research, 2017, vol. 74, # 6, p. 1699 - 1709
[8] Patent: WO2008/74835, 2008, A1, . Location in patent: Page/Page column 75
[9] Patent: US2012/220767, 2012, A1, . Location in patent: Page/Page column 8-9
[10] Patent: WO2007/130075, 2007, A1,
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  • [ 40003-41-6 ]
Reference: [1] Roczniki Chemii, 1972, vol. 46, p. 1647 - 1658
[2] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1722 - 1729[3] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1722 - 1729,8
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Reference: [1] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 763 - 768
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YieldReaction ConditionsOperation in experiment
98.39% With sodium carbonate In ethanol; ethyl acetate at 45 - 65℃; 200 ml of 25percent ethyl acetate in ethanol was added to the four-necked bottle, 30.4 g of thiourea, 1.5 g of sodium carbonate were added, and the temperature was raised to 45 ° C.33 g of ethyl 2-chloroacetoacetate was added dropwise, and the mixture was added dropwise over 20 to 30 minutes. The temperature was raised to 65 ° C for 5 hours, and most of the solvent was distilled off under normal pressure and then cooled to room temperature.The unreacted thiourea was removed by filtration, the filtrate was added to 500 ml of water, and the pH was adjusted to 9-10 with 30percent liquid alkali, and stirred for 0.5 h.After suction filtration and vacuum drying for 2 hours, the product was 36.7 g, and the yield was 98.39percent.
91.4% Reflux The 11.3 g, 84 mmol of thionyl chloride was added dropwise over 30 minutes previously cooled to 0 ° C containing 10 g, 76.9mmol of ethyl acetoacetate in 100 ml methylene chloride solution. After completion of stirring at room temperature overnight, thereaction solution respectively saturated sodium bicarbonate and saturated sodium chloride solution, the organic layer wascollected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 12.4 g of pink oil of ethyl 3-acetyl VII chloroacetate, 98.4percent yield, 3- acetyl acid ethyl ester VII prepared by the amount corresponding scaled up or down thevolume of the reaction vessel according to the corresponding scaled up or down, a commercially available compound VII havethe same effect; in 100 ml round-bottomed flask, 40 ml of ethanol and thiourea 2.0 g, 33.5 mmol, stirred and heated to refluxthiourea dissolved, add 5.5 g, 33.5 mmol 3- acetyl acid ethyl ester VII, after reflux overnight and concentrated under reducedpressure to remove ethanol to give a yellow solid, saturated with carbonate after filtration and washing soda solution of 5.3 g of2-amino-4-methyl-5-ethyl thiazole VIII, a yield of 91.4percent, 2-amino-4-methyl-5-ethyl thiazole VIII prepared by the amountcorresponding scaled up or down the volume of the reaction vessel according to the corresponding scaled up or down, acommercially available compound VII have the same effect.
91% at 70 - 80℃; for 0.25 h; In anhydrous ethanol (100 mL), thiourea (0.098 M) was added and stirred at room temperature. To this solution ethyl-2-chloro acetoacetate (0.097 M) was added dropwise under constant stirring at room temperature. Once addition of ethyl-2-chloro acetoacetate is complete, reaction mixture was heated at 70-80°C for 15 min. Then reaction mass was cooled to room temperature and the solid precipitate was isolated, washed with 100 mL of ethanol and further washed with saturated sodium bicarbonate solution to obtain white solid which was finally dried under vacuum at 50°C for 8 h Yield: 91percent; m.p.: 170-174°C; IR (KBr v max): 3357, 3055, 1741, 1680 1492, 1388, 913, 728 cm-1; 1H-NMR (300 MHz, DMSO-d6, δ, ppm): 1.37 (d, 3H, J = 7.2 Hz, CH3), 2.49 (s, 3H, CH3), 4.38 (q, 2H, J = 7.2 Hz, CH2CH3), 5.18 (bs, 2H, D2O exchangeable NH2); 13C-NMR (75 MHz, CDCl3, δ, ppm): 13.91, 17.32 (CH3), 61.71, 119.06, 157.47, 163.55 (C=O), 170.95 (C-NH2, thiazole); ESI-MS: m/z 187.19 (M+H); Analysis: calcd. for C7H10N2O2S: C,45.15; H,5.41; N,15.04percent; found: C, 45.14; H, 5.43; N, 15.07percent.
64% for 3 h; Reflux To a solution of 2-chloro-3-oxo-butyric acid ethyl ester (5 g, 0.030 mol, 1 eq) in ethanol (25 mL) was added thiourea (2.55 g, 0.033 mmol, 1.1 eq) at 25 °C, and the reaction mixture was heated at reflux for 3 h. Then reaction mixture was gradually cooled to 25 °C with stirring to precipitate the product as a white solid. The precipitated solid was collected by filtration using a Buckner funnel and dried under vacuum to obtain ethyl 2-amino-4- methylthiazole-5-carboxylate (4.8 g, 64percent) as a fine white powder.
64.8%
Stage #1: at 30℃; for 0.0833333 h;
Stage #2: With pyridine In ethanol at 30℃; for 6 h; Heating / reflux
Step; 1 Preparation of ethyl 2-amino-4-methyl-l,3-thiazoIe-5-carboxylateTo a solution of 2-chloro-ethyl acetoacetate (0.82g, 5mmol) in EtOH (25ml) was added thiourea (0.38gm, 5mmol) and the reaction mixture was stirred for 5 minutes at 3O0C. Pyridine (0.08g, lOmmol) was later added to the reaction mixture at 3O0C and the stirring was continued at reflux temperature for 6 hours. Subsequently the reaction mixture was diluted with ethyl acetate: hexane mixture (1:1, 10OmL) and filtered. After washing with diethyl ether (5OmL x 3), the crude material was purified by column chromatography using 1percent MeOH in dichloromethane as an eluent to give the product (0.61g, 64.8percent yield) as a white colored solid. Remaining steps were all performed according to the procedure given in example 1 to afford the title compound.
38% With sodium carbonate In tetrahydrofuran; acetonitrile at 120℃; for 0.5 h; Microwave irradiation To a stirred solution of ethyl 2-chloroacetoacetate (6.0 mL, 43.35 mmol) in MeCN (24 mL) and THF (6 mL) was added thiourea (3.0 g, 39.41 mmol) and Na2CO3 (0.417 g, 39.41 mmol). The reaction mixture was heated at 1200C under microwave irradiation for 30 minutes, cooled to r.t., partitioned between EtOAc and water, and the organic fraction was dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2.76 g, 38percent) as a cream solid. δH (CDCl3) 5.47 (2H, br. s), 4.27 (2H, q, J 7.2 Hz), 2.53 (3H, s), 1.33 (3H, t, J 7.2 Hz). MS (ES+) 187.0 (M+H)+.

Reference: [1] Patent: CN108570017, 2018, A, . Location in patent: Paragraph 0030; 0031; 0033; 0035; 0037
[2] Chemical Biology and Drug Design, 2016, vol. 87, # 4, p. 508 - 516
[3] Patent: CN102942565, 2016, B, . Location in patent: Paragraph 0028-0031; 0087-0088
[4] Archiv der Pharmazie, 2017, vol. 350, # 2,
[5] Acta Poloniae Pharmaceutica - Drug Research, 2017, vol. 74, # 6, p. 1699 - 1709
[6] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187
[7] Tetrahedron, 1994, vol. 50, # 24, p. 7253 - 7264
[8] Monatshefte fur Chemie, 2009, vol. 140, # 2, p. 209 - 211
[9] Patent: WO2017/152032, 2017, A1, . Location in patent: Paragraph 00452
[10] Patent: WO2007/113644, 2007, A2, . Location in patent: Page/Page column 18
[11] Patent: WO2008/47109, 2008, A1, . Location in patent: Page/Page column 38
[12] Justus Liebigs Annalen der Chemie, 1889, vol. 250, p. 289
[13] Synlett, 1999, # 8, p. 1239 - 1240
[14] Patent: WO2010/7482, 2010, A2, . Location in patent: Page/Page column 22-23
[15] Patent: WO2011/73617, 2011, A1, . Location in patent: Page/Page column 25
[16] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 445 - 453
[17] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1625 - 1629
[18] Phosphorus, Sulfur and Silicon and the Related Elements, 2018, vol. 193, # 3, p. 164 - 167
[19] Patent: CN101921268, 2016, B, . Location in patent: Paragraph 0128; 0131; 0132-0135
[20] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 49 - 60
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YieldReaction ConditionsOperation in experiment
98% With montmorillonite K10 Clay; iodine In dimethyl sulfoxide at 80℃; for 2 h; Green chemistry General procedure: A mixture of methylcarbonyl (0.5 mmol), thiourea (0.5 mmol), iodine (0.5 mmol), DMSO (2 mL) and 20 mg MMT-K10 was stirred at 80 °C. After completion of the reaction (monitored by TLC, petroleum:ethyl acetate, 4:1), the catalyst was separated by filtration, and then the solvent was removed under reduced pressure. The crude product was dissolved in hot water, extracted with ether (3 9 30 mL), and adjusted to pH = 9–10 by ammonia to give the solid products. Finally, the resulting precipitate was recrystallyzed by EtOH.
96% With iodine In dimethyl sulfoxide at 80℃; for 1 h; Green chemistry General procedure: A mixture of methylcarbonyl (0.5 mmol), thiourea(0.5 mmol), iodine (0.5 mmol), DMSO (2 mL) and 10 mgStarch NPs were stirred at 80 C. After completion of thereaction (monitored by TLC, petroleum:ethyl acetate, 4:1),the reaction was quenched by the addition of 10 mL distilledwater. The aqueous solution was extracted withEtOAc (3 9 10 mL) and the combined extract was driedwith anhydrous Na2SO4. The solvent was vacuumed, andfinally, the resulting precipitate was recrystallized byEtOH.
95% With N-iodo-succinimide In ethanol at 20℃; for 1.5 h; General procedure: A mixture of methyl carbonyl (2 mmol), thiourea (3 mmol), NIS(2 mmol), and NH2-MMT (0.10 g) in EtOH (5 mL) at room temperature was stirred until completion of reaction. The progress of the reaction was monitored by TLC (petroleum ether-ethyl acetate 4:1). After completion of the reaction, the NH2-MMT was separated by filtration. After evaporation of EtOH under vacuum, the crude product was dissolved in boiling water and adjusted to pH 8 withthe amount of ammonia to give the solid products. The solid obtained was recrystallized from a mixture of ethanol-water.
93% With N-Bromosuccinimide; sodium p-sulfonatocalix[6]arene In water; acetone at 20℃; for 1 h; To a 50 ml round bottom flask was added 20 ml of water,Then will be 1.5mmo 1 of the sulfonated cup [6] is added to the round bottom flaskAnd stir to make it completely soluble in water,To obtain a sulfonated cup [6] aqueous solution;3 mmol of ethyl acetoacetate was dissolved in 2 ml of acetone and mixed well,To give the mixture N1; the mixture N1 was slowly dropped into the sulfonated cup [6] aromatic aqueous solution at a rate of 60 drops / min,Followed by the addition of 0.03 mmol of N-bromosuccinimide and 3 mmo of thiourea at 20 ° C for lh;Finally, the reaction mixture was successively extracted by ethyl acetate, dried over anhydrous sodium sulfate,Vacuum distillation and column chromatography (mobile phase ethyl acetate: petroleum ether = 1:10, stationary phase silica gel)Get 52gAmine thiazole pentad heterocyclesCompoundsA1,The yield was 93percent
90% With iodine In ethanol for 3 h; Reflux General procedure: A mixture of the acetophenone (2 mmol), thiourea (3 mmol) and iodine (2 mmol), in the presence of 0.03 g nanochitosan was refluxed in EtOH.
The progress of the reaction was monitored by TLC (petroleum ether-ethyl acetate 4:1).
After completion of the reaction, the catalyst was separated by simple filtration.
After evaporation of solvent, the crude product was dissolved in boiling water, extracted with ether (3 * 30 mL), and adjusted to pH = 8 with the amount of ammonia to give the solid products.
The solid was recrystallized with ethanol-water to give pure 2-aminothiazole.
78% With tert.-butylhydroperoxide; 2,2'-azobis(isobutyronitrile) In methanol at 20 - 65℃; General procedure: General procedure: The substrate 1 (1.0 mmol) and thiourea 2(2.0 mmol) were added to solvent (5 mL methanol) at room tem-perature. To the reaction mixture, TBHP (3.0 mmol) and AIBN(0.2 mmol) were added respectively. The reaction mixture wasstirred at room temperature (for substrates 1a-f) or reux tem-perature (for substrates 1g-r) until TLC indicated the total consumption of 1 (for substrates 1p-q, the reaction time is 24 h).The residue was treated with saturated aqueous NaHCO3 (50 mL)and then extracted with EA (30 mL 3). The organic phase waswashed with brine (50 mL 1), dried over anhydrous Na2SO4. Thesolvent was removed and the residue was puried by ash columnchromatography on silica gel (EA/PE) to afford the desired compound 3.
66%
Stage #1: With tribromo-isocyanuric acid In water at 70℃; for 0.333333 h;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In water; acetonitrile at 70℃; for 0.333333 h;
General procedure: To a solution of the appropriate β-keto ester (1 mmol) in H2O (5 mL)held at 70 °C was added TBCA (146 mg, 0.4 mmol) in small portions and the mixture was stirred at 70 °C for 20 min. Then, MeCN (5 mL),the respective thiourea (1 mmol), and DABCO (1 mmol) were successively added and the mixture was stirred at 70 °C for an additional 20min. After the completion of the reaction, the mixture was poured onto ice and the precipitated solid was collected by filtration to afford the corresponding pure 2-aminothiazole 1.

Reference: [1] RSC Advances, 2016, vol. 6, # 69, p. 64749 - 64755
[2] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 8175 - 8183
[3] Letters in Organic Chemistry, 2011, vol. 8, # 8, p. 549 - 553
[4] Monatshefte fur Chemie, 2017, vol. 148, # 4, p. 745 - 749
[5] Journal of Molecular Structure, 2017, vol. 1144, p. 58 - 65
[6] Patent: CN104672167, 2016, B, . Location in patent: Paragraph 0053-0054
[7] Applied Organometallic Chemistry, 2016, vol. 30, # 12, p. 1043 - 1049
[8] Synthesis, 2007, # 22, p. 3469 - 3472
[9] Catalysis Communications, 2016, vol. 77, p. 108 - 112
[10] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 966
[11] Tetrahedron, 2018, vol. 74, # 17, p. 2107 - 2114
[12] Synthesis (Germany), 2018, vol. 50, # 24, p. 4867 - 4874
[13] Journal of the American Chemical Society, 1945, vol. 67, p. 2242[14] Journal of the American Chemical Society, 1946, vol. 68, p. 871
[15] Agricultural and Biological Chemistry, 1981, vol. 45, # 5, p. 1129 - 1134
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[17] Research on Chemical Intermediates, 2017, vol. 43, # 11, p. 6207 - 6231
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YieldReaction ConditionsOperation in experiment
78% With bromine; thiourea In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; ethanol; water EXAMPLE 22A
ethyl 2-amino-4-methylthiazole-5-carboxylate
A 50 mL round-bottom flask was charged with ethyl acetoacetate (6.4 mL, 50 mmol) and water (25 mL).
Bromine (2.8 mL, 51 mmol) was added over 30 minutes and an orange solution formed.
The reaction was added to diethyl ether (100 mL).
The organic layer was dried (MgSO4) and solvent removed under vacuum.
The remaining orange gel was added to a refluxing solution of thiourea (8.95 g, 117.5 mL) in ethanol (25 mL).
The reaction was refluxed for approximately 2 hours, cooled slightly, and poured into 50 mL of ice water.
The pH was adjusted to ca.7-9 with NH40H. A thick white precipitate formed.
The mixture was filtered to collect the solid.
The product was recrystallized from 95percent EtOH to provide 7.3 g (78percent) of the title compound as a white, fluffy crystalline solid.
1H NMR (300 MHz, CDCl3) δ 4.6, q, 3H; 2.55, s, 3H; 1.35, t, 2H; MS (DCI/NH3) m/z 187 (M+H)+.
Reference: [1] Patent: US6277871, 2001, B1,
[2] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187
[3] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1722 - 1729[4] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1722 - 1729,8
[5] Patent: CN102942565, 2016, B,
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 7840 - 7855
[7] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1625 - 1629
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2018, vol. 193, # 3, p. 164 - 167
[9] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 49 - 60
[10] Green Chemistry, 2018, vol. 20, # 24, p. 5464 - 5468
  • 9
  • [ 84911-18-2 ]
  • [ 17356-08-0 ]
  • [ 7210-76-6 ]
Reference: [1] Pharmaceutical Chemistry Journal, 2001, vol. 35, # 2, p. 96 - 98
[2] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1722 - 1729[3] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1722 - 1729,8
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 7840 - 7855
  • 10
  • [ 28465-06-7 ]
  • [ 7210-76-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 24, p. 5464 - 5468
[2] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442
[3] Journal fuer Praktische Chemie (Leipzig), 1970, vol. 312, p. 359 - 365
  • 11
  • [ 84911-18-2 ]
  • [ 7210-76-6 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5265 - 5269
  • 12
  • [ 609-15-4 ]
  • [ 7210-76-6 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5265 - 5269
  • 13
  • [ 141-97-9 ]
  • [ 17356-08-0 ]
  • [ 53266-94-7 ]
  • [ 7210-76-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 763 - 768
  • 14
  • [ 141-97-9 ]
  • [ 1071-86-9 ]
  • [ 7210-76-6 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 1813
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 1813
  • 15
  • [ 626-34-6 ]
  • [ 7210-76-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442
[2] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442
  • 16
  • [ 28241-61-4 ]
  • [ 141-97-9 ]
  • [ 7210-76-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1970, vol. 312, p. 359 - 365
  • 17
  • [ 46124-79-2 ]
  • [ 141-97-9 ]
  • [ 7210-76-6 ]
Reference: [1] Indian Journal of Chemistry, 1967, vol. 5, p. 216 - 218
  • 18
  • [ 105-39-5 ]
  • [ 17356-08-0 ]
  • [ 7210-76-6 ]
Reference: [1] Indian Journal of Chemistry, 1967, vol. 5, p. 216 - 218
  • 19
  • [ 409317-77-7 ]
  • [ 100-63-0 ]
  • [ 7210-76-6 ]
Reference: [1] Chemische Berichte, 1952, vol. 85, p. 1077,1083
  • 20
  • [ 70700-53-7 ]
  • [ 100-63-0 ]
  • [ 7210-76-6 ]
Reference: [1] Chemische Berichte, 1952, vol. 85, p. 1077,1083
  • 21
  • [ 540-80-7 ]
  • [ 7210-76-6 ]
  • [ 7238-62-2 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride In water; acetonitrile B.
Ethyl 2-chloro-4-methyl-5-thiazolecarboxylate
To a mixture of t-butyl nitrite (8.30 g, 80 mmol), cuprous chloride (6.38 g, 65 mmol) in 400 mL of acetonitrile was added Ethyl 2-Amino-4-methyl-5-thiazole-carboxylate (10 g, 54 mmol) in one portion.
The thiazole dissolved after 25 minutes, and the reaction was allowed to stir at room temperature for 2 hours.
The temperature was then increased to 66° C. for one hour.
The solution was gradually allowed to cool to room temperature and filtered.
The filtrate was poured into 400 mL of 6N HCl (the solution began fizzing).
The solution was strirred for 20 minutes at which time TLC analysis showed that all of the starting material had been consumed and one product formed.
The aqueous mixture was diluted with 700 mL of H2O and then extracted with ethyl acetate (4*400 mL).
The ethyl acetate fractions were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 10.45 g (94percent yield) of a reddish oil which crystallized to a reddish-orange solid: 1H NMR (CDCl3) δ4.35 (q, 2H), 2.7 (s, 3H), 1.35 (t, 3H).
Reference: [1] Patent: US6413997, 2002, B1,
  • 22
  • [ 540-80-7 ]
  • [ 7210-76-6 ]
  • [ 7732-18-5 ]
  • [ 7238-62-2 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride In acetonitrile B.
Ethyl 2-chloro-4-methyl-5-thiazolecarboxylate
To a mixture of t-butyl nitrite (8.30 g, 80 mmol), cuprous chloride (6.38 g, 65 mmol) in 400 mL of acetonitrile was added Ethyl 2-Amino-4-methyl-5-thiazole-carboxylate (10 g, 54 mmol) in one portion.
The thiazole dissolved after 25 minutes, and the reaction was allowed to stir at room temperature for 2 hours.
The temperature was then increased to 66° C. for one hour.
The solution was gradually allowed to cool to room temperature and filtered.
The filtrate was poured into 400 mL of 6N HCl (the solution began fizzing).
The solution was strirred for 20 minutes at which time TLC analysis showed that all of the starting material had been consumed and one product formed.
The aqueous mixture was diluted with 700 mL of H2 O and then extracted with ethyl acetate (4*400 mL).
The ethyl acetate fractions were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 10.45 g (94percent yield) of a reddish oil which crystallized to a reddish-orange solid: 1 H NMR (CDCl3) 67
4.35 (q, 2H), 2.7 (s, 3H), 1.35 (t, 3H).
Reference: [1] Patent: US6096898, 2000, A,
  • 23
  • [ 7210-76-6 ]
  • [ 7238-62-2 ]
Reference: [1] Journal of medicinal chemistry, 1969, vol. 12, # 3, p. 553 - 553
  • 24
  • [ 7210-76-6 ]
  • [ 22900-83-0 ]
YieldReaction ConditionsOperation in experiment
87% With nitrous acid isobutyl ester; trimethylsilyl bromide In ethyl acetate; acetonitrile at 0 - 20℃; for 24 h; TO A SOLUTION OF 2-METHYL-1-NITROSOOXY-PROPANE (28.2 ML, 2.1 EQ. ) IN CH3CN (700
ML) COOLED TO 0XB0;C WAS ADDED DROPWISE BROMO-TRIMETHYL-SILANE (32 ML, 2.1 EQ. ). THE] resulting mixture was maintained at [0XB0;C.] A solution of the available 2-amino-4- methyl-thiazole-5-carboxylic acid ethyl ester (18.6 g, 0.1 mol) in CH3CN/AcOEt 75/25 was added dropwise and the reaction mixture was maintained at [0XB0;C.] The mixture was stirred for 24 hours at rt. The solvent was evaporated and water was added. The product was extracted with AcOEt, dried over [NA2SO4,] filtered and evaporated. The title compound was obtained as a yellow solid (21.74 g, 87 [MMOL)] in 87percent yield after purification by flash chromatography using DCM as eluent ; GC/MS: [M'C7H8BRNO2S] 250.
87%
Stage #1: With nitrous acid isobutyl ester; trimethylsilyl bromide In acetonitrile at 0℃; for 0.333333 h;
Stage #2: at 0 - 55℃; for 0.0458333 h;
A solution of 2-methyl-1-nitrosooxy-propane (28.2 ml, 2.1 eq.) in CH3CN (700 ml) was cooled to 0C and bromo-trimethyl-silane (32 ml, 2.1 eq.) was added dropwise over 20 min. A solution of the available 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (18.6 g, 0.1 mot) in a mixture CH3CN/EtOAc : 75/25 heated to 55C was added dropwise over 45 min. During the addition the reaction was maintained at 0C and then allowed to warm to rt and stirred for 2 hours. After evaporation, the product was extracted with AcOEt, washed with water, dried over Na2SO4, filtered and evaporated. The title compound was obtained as a yellow solid (21.74 g, 86.96 mmol) in a 87percent yield; GC/MS : M+ C7H6BrNO2S 250.
85% With nitrous acid isobutyl ester; trimethylsilyl bromide In ethyl acetate; acetonitrile at 0 - 20℃; for 2.75 h; A solution of 2-methyl-1-nitrosooxypropane (20 [ML,] 2 eq) in CH3CN (700 mL) was [COOLED TO 0°C AND BROMO-TRIMETHYL-SILANE (20 ML, 2 EQ. ) WAS ADDED DROPWISE OVER 20] min. The available 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (14.0 g, 75.2 [MMOL)] in a mixture of CH3CN/EtOAc [(75/25)] at [55°C] was added dropwise over 45 min. During the addition the reaction was maintained at [0°C.] After return at rt, the mixture was stirred for 2 hours. After evaporation, the product was extracted with DCM, washed with water, dried over [NA2SO4,] filtered and evaporated off. The title compound was obtained as a pale orange solid (16.06 g, 75.2 [MMOL)] in a 85percent yield ; GC/MS: [M+ C7H8BRNO2S] 250
83%
Stage #1: With n-Amyl nitrite In acetonitrile at 60℃; for 4 h;
Stage #2: With water; sodium hydroxide In acetonitrile at 10 - 35℃;
A solution of copper(II) bromide (3.6 g, 16.11 mmol) and n-amyl nitrite (1.07 mL, 8.06 mmol) in acetonitrile (22 mL) was heated to 60°C, and a solution of ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate (1.0 g, 5.37 mmol) in acetonitrile (30 mL) was added dropwise thereto.
The mixture was stirred for 4 hr at same temperature.
The reaction mixture was allowed to cool to room temperature, and added into ice-cooled 1N aqueous sodium hydroxide solution.
The mixture was extracted with ethyl acetate.
The organic layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (hexane:ethyl acetate= 95:5→85:15) to give the title compound (1.1 g, 83percent).
1H-NMR (CDCl3) δ : 1.37 (3 H, t, J = 7.1 Hz), 2.72 (3 H, s), 4.33 (2 H, q, J = 7.1 Hz).
76% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0℃; for 4 h; To a stirred solution of Intermediate 6 (0.53 g, 2.85 mmol) in MeCN (6 mL) at00C was added CuBr2 (0.70 g, 3.13 mmol) followed by dropwise addition of tert-buty\\ nitrite (0.44 mL, 3.70 mmol). After stirring at 00C for 4 h, the reaction mixture was concentrated in vacuo to give a black oil. Purification by column chromatography (SiO2, 0-50percent EtOAc/hexanes) gave the title compound (0.54 g, 76percent) as a yellow solid. 6H (CDCl3) 4.33 (2H, q, J 7.0 Hz), 2.71 (3H, s), 1.36 (3H, t, J 7.2 Hz). MS (ES+) 252.0 (M+H)+.
62% With potassium bromide; copper(I) bromide; sodium nitrite In water at 60℃; for 1 h; Compound 3 (1 mmol) in HBr (3 mL) was added to cold aqueous solution of CuBr (1 mmol) and KBr(0.2 mmol) followed by dropwise addition of preliminary cooled aqueous solution of NaNO2(10 mL) for 1 h. The reaction mixture was stirred at 60°C for 2 h. The reaction progress was monitored byTLC until the starting material completely disappeared.The reaction mixture was diluted with water,the obtained precipitate was filtered off to give ethyl 2-bromo-4-methylthiazole-5-carboxylate 4 as off-whitesolid in 62percent yield. 1H NMR spectrum (CDCl3), δ,ppm: 4.28 q (2H), 2.81 s (3H), 1.33 t (3H). Massspectrum (ESI-MS): m/z 251 [M + H]+.
59% With copper(I) bromide; isopentyl nitrite In acetonitrile at 80℃; for 4 h; To a suspension of ethyl 2-amino-4-methylthiazole-5-carboxylate (1 g, 5.36 mmol, 1 eq) and CuBr2 (1.19 g, 5.36 mol, 1 eq) in acetonitrile (25 mL) was added isoamyl nitrite (2.16 mL, 16.08 mmol, 3 eq) dropwise at 25 °C, and the reaction mixture was stirred at 80°C for 4 h. The resulting reaction mixture was gradually cooled to 25 °C and concentrated under reduced pressure to remove excess isoamyl nitrite and acetonitrile. The residue obtained was partitioned between water (250 mL) and ethyl acetate (250 mL), and the organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure to obtain the crude compound as a brownish solid. The crude product obtained was purified by silica gel (23 0-400) column chromatography (10percent ethyl acetate in hexane) to obtain ethyl 2-bromo-4-methylthiazole- 5-carboxylate (800 mg, 59percent) as a yellow solid.

Reference: [1] Patent: WO2004/6923, 2004, A1, . Location in patent: Page/Page column 38
[2] Patent: WO2004/6924, 2004, A1, . Location in patent: Page/Page column 31-32
[3] Patent: WO2004/7493, 2004, A1, . Location in patent: Page 24-25
[4] Patent: EP2518054, 2012, A1, . Location in patent: Page/Page column 53
[5] Patent: WO2008/47109, 2008, A1, . Location in patent: Page/Page column 38
[6] Russian Journal of General Chemistry, 2016, vol. 86, # 7, p. 1722 - 1729[7] Zh. Obshch. Khim., 2016, vol. 86, # 7, p. 1722 - 1729,8
[8] Patent: WO2017/152032, 2017, A1, . Location in patent: Paragraph 00453
[9] Journal of medicinal chemistry, 1969, vol. 12, # 3, p. 553 - 553
[10] Roczniki Chemii, 1972, vol. 46, p. 1647 - 1658
[11] Patent: WO2011/73617, 2011, A1, . Location in patent: Page/Page column 25
[12] Chinese Chemical Letters, 2016, vol. 27, # 5, p. 703 - 706
[13] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1625 - 1629
  • 25
  • [ 7210-76-6 ]
  • [ 110-46-3 ]
  • [ 22900-83-0 ]
YieldReaction ConditionsOperation in experiment
70% With trimethylsilyl bromide In ethyl acetate; acetonitrile at 0 - 20℃; [2-BROMO-4-METHYL-THIAZOLE-5-CARBOXVLIC] acid ethyl ester To a solution of 3-methyl-1-nitrosooxy-butane (19.8 mL, 2.1 eq) in acetonitrile (700 mL) was added at [0XB0;C] trimethylsillyl bromide (19.6 mL, 2.1 eq) and the mixture was stirred at [0XB0;C] for 20 min. A solution of 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester (14.0 g, 1.0 eq) in acetonitrile/EtOAc : 75/25 (700 mL) was added slowly at [0XB0;C.] After stirring overnight at rt, the reaction mixture was evaporated and purified by flash chromatography to give the title compound (13.2 g, 0. [051MOL)] as an orange solid in a 70percent yield ; GC/MS: [M C7H8BRNO2S] 250;'H NMR [(CDC13,] 300 MHz) 5 4.32 (q, 2H), 2.69 (s, 3H), 1.34 (t, 3H)
Reference: [1] Patent: WO2004/6922, 2004, A1, . Location in patent: Page/Page column 34; 35
  • 26
  • [ 7210-76-6 ]
  • [ 63788-62-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1977, p. 908 - 912
[2] Patent: US2012/220767, 2012, A1,
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7578 - 7583
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