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[ CAS No. 127942-30-7 ] {[proInfo.proName]}

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Chemical Structure| 127942-30-7
Chemical Structure| 127942-30-7
Structure of 127942-30-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 127942-30-7 ]

CAS No. :127942-30-7 MDL No. :MFCD06653384
Formula : C6H9BrN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :KQLKNNNNKWTAMQ-UHFFFAOYSA-N
M.W : 253.12 Pubchem ID :16495520
Synonyms :

Calculated chemistry of [ 127942-30-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.64
TPSA : 93.45 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
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) : 0.0
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.36
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.86
Solubility : 0.348 mg/ml ; 0.00138 mol/l
Class : Soluble
Log S (Ali) : -3.72
Solubility : 0.0478 mg/ml ; 0.000189 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.41
Solubility : 9.8 mg/ml ; 0.0387 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.66

Safety of [ 127942-30-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 127942-30-7 ]

* 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.

  • Downstream synthetic route of [ 127942-30-7 ]

[ 127942-30-7 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 70-23-5 ]
  • [ 62-56-6 ]
  • [ 127942-30-7 ]
YieldReaction ConditionsOperation in experiment
98% In ethyl acetate at 60 - 110℃; Cooling; 6.1 Step 1: Preparation of 2-amino-thiazole-4-carboxylic acid ethyl ester hydrobromide To a 3 L 3 neck flask fitted with a condenser, thermometer, and mechanical stirred, set in an oil bath, was charged with thiourea (48.2 g, 634 mmol) and ethyl bromopyruvate (137 g, 88.3mL, 634 mmol). The reaction was heated slowly and carefully until a clear solution formed(60°C) upon which the reaction became exothermic (temperature of reaction reached 110°C) andwas stirred as the reaction solidified. To the reaction was added EA (500 mL), the reaction wasremoved from heat and cooled to room temperature. The solid was filtered and washed with EA and Et2O resulting in 2-amino-thiazole-4-carboxylic acid ethyl ester hydrobromide salt resultingin a white solid (157 g, 98% ).
90% In ethanol at 78℃; for 1h;
87% at 100℃; for 1h;
at 100℃; for 1h; 7.m.i (m) 3-[(2-Phenyl-thiazole-4-carbonyl)-amino]-phenylj-acetic acid (54); (i) 2-Amino-thiazole-4-carboxylic acid ethyl ester hydrobromide salt; Thiourea (1.5 g, 20 mmol) and ethyl bromopyruvate (2.8 ml, 22 mmol) were heated at 100°C for 1 h. The reaction was cooled and acetone (10 ml) was added. The mixture was then filtered to give a yellow/brown solid and the crude material was crystallised from hot ethanol (20 ml) to give the title compound as the HBr salt (2.63 g). The liquor was concentrated and recrystallised from hot EtOH (5 ml) to give further product (0.63 g). Yield: 3.26 g, 64% ; LC/MS tr 0.67 min; MS (ES+) m/z 173 (M+H) ; 1H NMR (400 MHz, MeOD) 5 1.42 (t, 3H), 4.43 (q, 2H), 7.74 (s, 1H).
at 100℃; for 1h;
In ethanol for 2h; Heating / reflux;
In ethanol for 2h; Reflux; 5.1.35. Ethyl 2-amino-1,3-thiazole-4-carboxylate hydrobromide (37) A mixture of 36 (100 g), thiourea (39 g) and EtOH (500 mL) was refluxed for 2 h. The reaction mixture was concentrated in vacuo. The crystalline residue was collected and washed with AcOEt to give 37 (116 g, 131%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 1.28 (3H, t, J = 7 Hz), 4.26 (2H, q, J = 7 Hz), 7.60 (1H, s).

  • 2
  • [ 127942-30-7 ]
  • [ 100367-77-9 ]
  • [ 208264-60-2 ]
YieldReaction ConditionsOperation in experiment
1: 1.83 g 2: 88% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 2h;
  • 3
  • [ 1885-14-9 ]
  • [ 127942-30-7 ]
  • [ 232596-68-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine In tetrahydrofuran
  • 4
  • [ 1378831-76-5 ]
  • [ 62-56-6 ]
  • [ 127942-30-7 ]
YieldReaction ConditionsOperation in experiment
In acetone at 100℃; for 0.75h; 26 EXAMPLE 26; 4-(4-Ethoxycarbonyl-thiazol-2-yl)-phenyl-ammonium chloride Thiourea (7.60 g, 100 MMOL) and ethyl bromopyruvate (12.6 mL, 100 MMOL) were mixed and heated to 100 C for 45 min. After cooling of the reaction mixture, the solid obtained was triturated with acetone, filtered and recrystallized from EtOH to obtain the desired aminothiazole product (10.6 g, 40 MMOL).
  • 5
  • [ 127942-30-7 ]
  • [ 1378831-76-5 ]
YieldReaction ConditionsOperation in experiment
85% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 2.5h; 26 EXAMPLE 26; 4-(4-Ethoxycarbonyl-thiazol-2-yl)-phenyl-ammonium chloride The aminothiazole was then added slowly (over a period of 20 min) to a solution of T-BUTYLNITRITE (6.2 g, 60 MMOL) and CuBr2 (10.7 g, 48 MMOL) IN MECN (160 mL) at 0 C. The reaction mixture was allowed to warm-up to RT and to stirred for 2.5 h. The mixture was then added to an aqueous HCI solution (20%) and extracted with Et2O (2 x 400 mL). The organic layer was washed with aqueous HCI (10%), dried OVER ANHYDROUS MGS04 and evaporated to dryness. The desired BROMOTHIAZOLE product was isolated in -85% yield (4.3 g) after flash column chromatography using 15% EtOAc in hexane as the eluent.
  • 6
  • [ 75-36-5 ]
  • 2-amino-4-ethoxycarbonyl-1,3-thiazolehydrobromide [ No CAS ]
  • [ 92819-12-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0℃; for 0.5h;
  • 7
  • [ 70-23-5 ]
  • [ 62-56-6 ]
  • [ 127942-30-7 ]
YieldReaction ConditionsOperation in experiment
at 100℃; for 0.75h; Heating / reflux; 12 Thiourea (7.60 g, 100 mmol) and ethyl bromopyruvate (12.6 mL, 100 mmol) were mixed and heated to 100° C. for 45 min. After cooling of the reaction mixture, the solid obtained was triturated with acetone, filtered and recrystallized from EtOH to obtain the desired aminothiazole product (10.6 g, 40 mmol). The aminothiazole was then added slowly (over a period of 20 min) to a solution of t-butylnitrite (6.2 g, 60 mmol) and CuBr2 (10.7 g, 48 mmol) in MeCN (160 mL) at 0° C. The reaction mixture was allowed to warm-up to RT and to stirred for 2.5 h. The mixture was then added to an aqueous HCl solution (20%) and extracted with Et2O (2×400 mL). The organic layer was washed with aqueous HCl (10%), dried over anhydrous MgSO4 and evaporated to dryness. The desired bromothiazole product was isolated in 85% yield (4.3 g) after flash column chromatography using 15% EtOAc in hexane as the eluent.
  • 8
  • [ 127942-30-7 ]
  • [ 100367-77-9 ]
YieldReaction ConditionsOperation in experiment
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 2.5h; 12 Thiourea (7.60 g, 100 mmol) and ethyl bromopyruvate (12.6 mL, 100 mmol) were mixed and heated to 100° C. for 45 min. After cooling of the reaction mixture, the solid obtained was triturated with acetone, filtered and recrystallized from EtOH to obtain the desired aminothiazole product (10.6 g, 40 mmol). The aminothiazole was then added slowly (over a period of 20 min) to a solution of t-butylnitrite (6.2 g, 60 mmol) and CuBr2 (10.7 g, 48 mmol) in MeCN (160 mL) at 0° C. The reaction mixture was allowed to warm-up to RT and to stirred for 2.5 h. The mixture was then added to an aqueous HCl solution (20%) and extracted with Et2O (2×400 mL). The organic layer was washed with aqueous HCl (10%), dried over anhydrous MgSO4 and evaporated to dryness. The desired bromothiazole product was isolated in 85% yield (4.3 g) after flash column chromatography using 15% EtOAc in hexane as the eluent.
  • 10
  • [ 127942-30-7 ]
  • [ 5398-36-7 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In water; ethyl acetate 7.m.ii (ii) 2-Chloro-thiazole-4-carboxylic acid ethyl ester; 2-Amino-thiazole-4-carboxylic acid ethyl hydrobromide salt (506 mg, 2 mmol) was converted to the free base by partitioning between aqueous saturated K2CO3 solution and EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to give the free base (306 mg, 89%).
In dichloromethane
  • 11
  • [ 70-23-5 ]
  • [ 127942-30-7 ]
YieldReaction ConditionsOperation in experiment
85% With thiourea 3.a a) a) ethyl 2-aminothiazole-4-carboxylate Hydrobromide To a stirring suspension of thiourea (46.7 g, 0.614 mol) in EtOH (640 mL) was added ethyl bromopyruvate (120 g, 0.614 mol, 77.2 mL) slowly. After stirring at 45° C. for 16 h the solution was cooled to room temperature and placed in the refrigerator overnight. The mixture was filtered, the crystals were washed with cold ethanol and air dried to give the product as pale yellow crystals (132.74 g, 85%). MS (ESI): 172.9 (M+H)+.
79% With thiourea In ethanol 5.a a a ethyl 2-aminothiazole-4-carboxylate hydrobromide To a stirring suspension of thiourea (6.0 g, 78.8 mmol) in ethanol (80 mL) was added ethyl bromopyruvate (15.4 g, 78.8 mmol). The resulting solution was heated at 45° C. for 23 hours. The solution was cooled at 0° C. for 24 hours, and the crystals were collected by filtration and washed with cold ethanol to provide the title compound (15.8 g, 79%). 1H NMR (400 MHz, CD3OD) d 7.70 (s, 1H), 4.41 (q, 2H), 1.38 (t, 3H).
79% With thiourea In ethanol 112.a a) a) ethyl 2-aminothiazole-4-carboxylate hydrobromide To a stirring suspension of thiourea (6.0 g, 78.8 mmol) in ethanol (80 mL) was added ethyl bromopyruvate (15.4 g, 78.8 mmol). The resulting solution was heated at 45° C. for 23 h. The solution was cooled at 0° C. for 24 h, and the crystals were collected by filtration and washed with cold ethanol to provide the title compound (15.8 g, 79%). 1 H NMR (400 MHz, CD3 OD) δ 7.70 (s, 1H), 4.41 (q, 2H), 1.38 (t, 3H).
  • 12
  • [ 1711-11-1 ]
  • [ 127942-30-7 ]
  • [ 206882-10-2 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine In tetrahydrofuran; water R.1.2 Step 2 Step 2 In 15 ml of dried tetrahydrofuran, 968 mg of 2-amino-4-ethoxycarbonyl-1,3-thiazolehydrobromide were suspended. To the suspension, 1.19 g of triethylamine were added. A solution of 3-cyanobenzoyl chloride dissolved in 3 ml of dried tetrahydrofuran was added dropwise to the resulting mixture under ice cooling, followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1), whereby 980 mg of 2-[N-(3-cyanobenzoyl)amino]-4-ethoxycarbonyl-1,3-thiazole were obtained as white crystals. Yield: 83%. Melting point: 203.0 to 204.5° C.
  • 13
  • [ 127942-30-7 ]
  • [ 100367-77-9 ]
  • [ 83553-47-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-4-ethoxycarbonyl-1,3-thiazolehydrobromide With hydrogenchloride In water at -5℃; Stage #2: With sodium nitrite In water at 0℃; for 2.5h; Stage #3: With potassium iodide In dichloromethane; water at 0℃; for 1.16667h; F.119.1 Step 1. Mixture of 2-iodo-thiazole-4-carboxylic acid ethyl ester and 2-bromo-thiazole-4-carboxylic acid ethyl ester To a 1 L, 3-necked round bottom flask was added 2-amino-thiazole-4-carboxylic acid ethyl ester hydrobromide (20 g, 79 mmol). This was diluted with water (150 mL) followed by conc. HCl (150 mL). This mixture was cooled to ~minus 5° C. Separately, 8.15 g of sodium nitrite was dissolved in 75 mL of water. A solution of sodium nitrite (8.15 g, 118.1 mmol) in water (75 mL) was slowly added dropwise over a 30 minute period. The mixture was stirred for approximately 2 h after the completion of the addition of the sodium nitrite solution while maintaining the reaction temperature at 0° C. To this mixture was added dropwise over 10 minutes a solution of potassium iodide (17.6 g, 106.0 mmol) in water (75 mL). During the addition, dichloromethane was added to maintain the fluidity of the reaction mixture. After 1 hour, the ice bath was removed. The mixture was extracted with dichloromethane (3*500 mL). The combined organic extracts were washed with 10% Na2S2O3 (2*250 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash column chromatography eluding with 10-75% dichloromethane in hexane to give a mixture of 2-iodo-thiazole-4-carboxylic acid ethyl ester and 2-bromo-thiazole-4-carboxylic acid ethyl ester (10.8 g). This material was used for the next step without further purification.
  • 14
  • [ 79-30-1 ]
  • [ 127942-30-7 ]
  • [ 737822-96-7 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine In dichloromethane for 0.5h; Cooling with ice; 5.1.36. Ethyl 2-(iso-butyrylamino)-1,3-thiazole-4-carboxylate (38a) To a mixture of 37 (2.0 g), pyridine (1.3 mL) and CH2Cl2 (20 mL) was added i-butyryl chloride (0.91 mL) in an ice-water bath, and the mixture was stirred for 30 min. To the mixture was then added saturated aqueous NaHCO3 (30 mL) and the organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crystalline residue was collected and washed with AcOEt to give 38a (1.3 g, 70%) as an off-white solid. 1H NMR (CDCl3) δ 1.30 (6H, d, J = 7 Hz), 1.40 (3H, t, J = 7 Hz), 2.57-2.73 (1H, m), 4.41 (2H, q, J = 7 Hz), 7.83 (1H, s), 8.98 (1H, s); FAB MS m/e (M+H)+ 243.
  • 15
  • [ 501-53-1 ]
  • [ 127942-30-7 ]
  • [ 737823-57-3 ]
YieldReaction ConditionsOperation in experiment
84% With pyridine In dichloromethane at 20℃; for 1h; Cooling with ice; 5.1.37. Ethyl 2-[(benzyloxy)carbonyl]amino}-1,3-thiazole-4-carboxylate (38b) To a mixture of 37 (5.0 g), pyridine (3.4 mL) and CH2Cl2 (50 mL) was added benzyloxycarbonyl chloride (3.1 mL) in an ice-water bath, and the reaction mixture was stirred at room temperature for an hour. The mixture was washed with saturated aqueous NaHCO3 (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crystalline residue was collected and washed with iPr2O to give 38b (5.1 g, 84%) as an off-white solid. 1H NMR (CDCl3) δ 1.48 (3H, t, J = 7 Hz), 4.38 (2H, q, J = 7 Hz), 5.27 (2H, s), 7.36-7.44 (5H, m), 7.82 (1H, s); FAB MS m/e (M+H)+ 307.
  • 16
  • [ 100-74-3 ]
  • [ 3173-56-6 ]
  • [ 127942-30-7 ]
  • [ 232595-09-4 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 6.2 Step 2: Preparation of 2-(3-benzyl-ureido)-thiazole-4-carboxylic acid ethyl ester To a reaction vessel containing 2-amino-thiazole-4-carboxylic acid ethyl ester hydrobromide salt (66.6 g, 263 mmol), 4-ethylmorpholine (60.7 g, 67.1 mL, 527 mmol), and anhydrousDMF (660 ml) was added benzyl isocyanate (42.1 g, 316 mmol), reaction stirred at room temperatureunder argon for 7 hr, more benzyl isocyanate ( 42.1 g, 316 mmol) was added, and reactionstirred at room temperature under argon overnight. The next day the reaction was concentrated2/3, diluted with water (1.6 L), and the resulting precipitate was filtered and suction dried overnight yielding 2-(3-Benzyl-ureido )-thiazole-4-carboxylic acid ethyl ester as an off white solid(146 g, 182%). NMR analysis suggested material was still wet with water and DMF and wasused as is.
  • 17
  • [ 127942-30-7 ]
  • [ 1246552-02-2 ]
YieldReaction ConditionsOperation in experiment
With bromine; sodium hydrogencarbonate In dichloromethane at 0℃; for 1h;
  • 18
  • [ 94-74-6 ]
  • [ 127942-30-7 ]
  • [ 1286391-50-1 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 16h; 14 Synthesis Example 14. Compound Represented by [Chemical Formula 18] After adding 4-(ethoxycarbonyl)thiazol-2-aminium bromide (76 mg, 1.2 eq.), EDC-HCl (72 mg, 1.5 eq.), DMAP (1.5 mg, 0.05 eq.) and Et3N (70 μL, 2 eq.) to a solution of 2-(4-chloro-2-methylphenoxy)acetic acid (50 mg, 0.25 mmol) in CH2Cl2 (1 mL) at 0° C. and stirring at room temperature for 16 hours, the reaction mixture was diluted with CH2Cl2 (2 mL) and washed with 15% HCl (1 mL). The aqueous layer was extracted once more with CH2Cl2 (2 mL) and the organic layer was dried with MgSO4 and concentrated under reduced pressure. The obtained crude residue was purified by silica gel column chromatography (hexane:ethylacetate:dichloroethane=10:1:2, volume ratio), affording a [Chemical Formula 18] compound as a white solid. (0147) White solid, mp: 154.0-155.0° C.; 1H NMR (400 MHz, CDCl3) δ 9.79 (br s, 1H), 7.90 (s, 1H), 7.19 (s, 1H), 7.13 (dd, J=2.4, 8.8 Hz, 1H), 6.72 (d, J=8.8 Hz, 1H), 4.73 (s, 2H), 4.41 (q, J=7.2 Hz, 2H), 2.31 (s, 3H), 1.4 (t, J=7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 166.9, 161.4, 156.6, 153.7, 142.1, 131.4, 129.1, 127.7, 127.0, 122.9, 113.2, 67.8, 61.7, 16.5, 14.5; HRMS (ESI-QTOF) m/z [M+Na]+ calcd for C15H15ClN2NaO4S 377.0333. found 377.0331.
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