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[ CAS No. 18640-74-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 18640-74-9
Chemical Structure| 18640-74-9
Chemical Structure| 18640-74-9
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Product Details of [ 18640-74-9 ]

CAS No. :18640-74-9 MDL No. :MFCD00005334
Formula : C7H11NS Boiling Point : -
Linear Structure Formula :- InChI Key :CMPVUVUNJQERIT-UHFFFAOYSA-N
M.W : 141.23 Pubchem ID :62725
Synonyms :

Calculated chemistry of [ 18640-74-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.57
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.5
TPSA : 41.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 3.24
Consensus Log Po/w : 2.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.421 mg/ml ; 0.00298 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.163 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.5
Solubility : 0.452 mg/ml ; 0.0032 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 18640-74-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18640-74-9 ]

* 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 [ 18640-74-9 ]

[ 18640-74-9 ] Synthesis Path-Downstream   1~83

  • 1
  • [ 18640-74-9 ]
  • [ 127164-64-1 ]
  • C34H58NO6PS [ No CAS ]
  • 2
  • [ 18640-74-9 ]
  • [ 130471-23-7 ]
  • C35H52NO6PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Representative, non-limiting examples of compounds of the present invention are: ... 2-Ethyl-4-methylthiazole Ethyl 2-(Formylamino)-4-thiazoleacetate 2-(Formylamino)-alpha-(methoxyimino)-4-thiazoleacetic acid 2-Amino-4-phenylthiazole hydrochloride monohydrate 2-Isobutylthiazole 2-Methyl-2-thiazoline 2-Methyl-2-oxazoline 2-Oxazolidone ...
  • 5
  • [ 558-37-2 ]
  • [ 201230-82-2 ]
  • [ 18640-74-9 ]
  • 1-[2-(2-methylpropyl)thiazol-4-yl]-4,4-dimethyl-1-pentanone [ No CAS ]
  • 1-[5-(3,3-dimethylbutyl)-2-(2-methylpropyl)thiazol-4-yl]-4,4-dimethyl-1-pentanone [ No CAS ]
  • 6
  • [ 558-37-2 ]
  • [ 201230-82-2 ]
  • [ 18640-74-9 ]
  • 1-[5-(3,3-dimethylbutyl)-2-(2-methylpropyl)thiazol-4-yl]-4,4-dimethyl-1-pentanone [ No CAS ]
  • 7
  • [ 558-37-2 ]
  • [ 201230-82-2 ]
  • [ 18640-74-9 ]
  • 1-[2-(2-methylpropyl)thiazol-4-yl]-4,4-dimethyl-1-pentanone [ No CAS ]
  • 8
  • [ 50915-95-2 ]
  • [ 18640-74-9 ]
  • 5-(2-methylenedecyl)-2-(2-methylpropyl)thiazole [ No CAS ]
  • 9
  • [ 115413-63-3 ]
  • [ 18640-74-9 ]
  • 5-(3-butyl-2-methyleneheptyl)-2-(2-methylpropyl)thiazole [ No CAS ]
  • 10
  • [ 18640-74-9 ]
  • (1-hexylheptylidene)cyclopropane [ No CAS ]
  • 5-(3-hexyl-2-methylenenonyl)-2-(2-methylpropyl)thiazole [ No CAS ]
  • 12
  • [ 625-98-9 ]
  • [ 18640-74-9 ]
  • 5-(3-fluorophenyl)-2-isobutylthiazole [ No CAS ]
  • 13
  • [ 591-50-4 ]
  • [ 18640-74-9 ]
  • [ 600732-10-3 ]
  • 14
  • [ 942189-39-1 ]
  • [ 18640-74-9 ]
  • [ 1093064-64-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; johnphos;palladium diacetate; In 1,4-dioxane; at 100℃; To a pressure tube were charged compound 1AJ (194 mg, 0.4 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), (2-biphenyl)-di-tert-butylphospine (12 mg, 0.1 mmol), C2CO3 (313 mg, 0.96 mmol) and the tube was evacuated under vacuum and backfilled with nitrogen. Dioxane (4 ml) was introduced, followed by <strong>[18640-74-9]2-isobutylthiazole</strong> (114 mul, 0.8 mmol). The tube was sealed and heated at 100 0C with stirring overnight. After cooling the reaction mixture was filtered through Celite, washed with ethyl acetate several times. Filtrate was concentrated and the residue was purified on silica gel. Elution with ethyl acetate in hexanes (0-30%) gave compound 2BA (124 mg).
  • 16
  • [ 106-38-7 ]
  • [ 18640-74-9 ]
  • [ 1127218-00-1 ]
  • 17
  • [ 624-31-7 ]
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  • [ 1127218-00-1 ]
  • 18
  • [ 29540-83-8 ]
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  • 19
  • [ 1191913-83-3 ]
  • [ 18640-74-9 ]
  • [ 1191913-96-8 ]
  • 20
  • N-(2-bromophenyl)-N-(4-methoxybenzyl)methacrylamide [ No CAS ]
  • [ 18640-74-9 ]
  • [ 1191914-03-0 ]
  • 21
  • [ 10178-53-7 ]
  • [ 18640-74-9 ]
  • [ 1191913-88-8 ]
  • 22
  • [ 884-90-2 ]
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  • [ 1186493-08-2 ]
  • 23
  • [ 351-70-2 ]
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  • [ 1186493-08-2 ]
  • 24
  • [ 100-39-0 ]
  • [ 18640-74-9 ]
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  • 25
  • [ 100-44-7 ]
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  • 26
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  • 27
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  • [ 1186493-10-6 ]
  • 28
  • [ 18712-15-7 ]
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  • [ 1156006-02-8 ]
  • 29
  • [ 701270-84-0 ]
  • [ 18640-74-9 ]
  • [ 1383542-45-7 ]
YieldReaction ConditionsOperation in experiment
33% A solution of <strong>[18640-74-9]2-isobutylthiazole</strong> (from Aldrich; 0.72 g; MW 141.25 ; 1.3 eq) in tetrahydrofuran (15 ML) was cooled TO-78C. Next, a solution of t-butyllithium (from Aldrich; 1.7M in pentane; 5.06 ml; 2.7 eq) was slowly added. The mixture was then stirred for 30 min AT-78C. Afterward, a solution of zinc (II) chloride (from Aldrich; 1.0 M in diethyl ether; 6.4 ml; 2.0 eq) was slowly added. The mixture was then warmed to ambient temperature and stirred for 30 min. Lastly, a solution OF TERT-BUTYL-4-[(2-BROMO- 1, 3-benzothiazol-6-yl) sulfonyl] tetrahydro-2H-pyran-4-carboxylate (1.5 g; MW 462. 38; prepared in accordance with Part C, Example 9) and bis (triphenylphosphine) dichloropalladium (from Aldrich, 0.11 g, MW 701.89, 0.05 eq added) in tetrahydrofuran (20 ml) was added. The resulting mixture was heated at reflux for 16 hr. The reaction was then quenched with a saturated ammonium chloride solution (20 ml). The aqueous layer was separated and extracted with ethyl acetate (2X25ML). The resulting organics were combined, washed with brine (2X50 ml), dried over sodium sulfate, and concentrated to form a dark oil. The oil was chromatographed on silica get (ethyl acetate/hexanes) to afford the desired compound as a tan solid (0. 55 g, 33% yield). LH NMR and LCMS confirmed the presence of the desired compound. The"equivalents" above indicate equivalents relative to the charged amount OF TERT-BUTYL-CARBOXYLATE.
  • 30
  • [ 18640-74-9 ]
  • [ 905300-73-4 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere; Under an argon atmosphere, a mixture of 2- (2-methylpropyl) thiazole (1.41 g, 10 mmol) and N-bromosuccinimide (1.95 g, 11 mmol) was dissolved in N, N-dimethylformamide (5.0 mL). And stirred at room temperature. After 18 hours, water and ethyl acetate were added to the reaction mixture. The organic layer was separated and a desiccant was added here. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 10/1) to obtain the desired 5-bromo-2- (2-methylpropyl) thiazole as a brown liquid (2.18 g). 9.9 mmol, 99%).
99% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere; Under argon atmosphere, a mixture of 2- (2-methylpropyl) thiazole (1.41 g, 10 mmol) and N-bromosuccinimide (1.95 g, 11 mmol) was dissolved in N, N-dimethylformamide (5.0 mL). And stirred at room temperature. After 18 hours, the reaction mixtureTo this was added water and ethyl acetate. The organic layer was separated and a desiccant was added here. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (hexaneSun / ethyl acetate = 10/1) and purified to the desired 5-bromo-2- (2-methylpropyl)) Thiazole was obtained as a brown liquid (2.18 g, 9.9 mmol, 99%).
87% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 3h; [00200] To a solution of <strong>[18640-74-9]2-isobutylthiazole</strong> (600 mg, 4.25 mmol) in DMF (2 niL) was added N-bromosuccinimide (1.134 g, 6.37 mmol). The mixture was stirred at room temperature for 3 hours then subjected to flash column chromatography using 10% ethyl acetate/hexane to give a yellow oil (815.2 mg, 87% yield). LCMS (Conditions C): Tr 3.51 min; (M+H)+: 219.90 (100%), 221.90 (100%).
87% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 3h; To a solution of <strong>[18640-74-9]2-isobutylthiazole</strong> (600 mg, 4.25 mmol) in DMF (2 niL) was added N-bromosuccinimide (1.134 g, 6.37 mmol). The mixture was stirred at room temperature for 3 hours then subjected to flash column chromatography using 10% ethyl acetate/hexane to give a yellow oil (815.2 mg, 87% yield). LCMS (Conditions C): Tr 3.51 min; (M+H)+: 219.90 (100%), 221.90 (100%)

  • 31
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  • [ 1207426-84-3 ]
  • 32
  • [ 292638-84-7 ]
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  • [ 1236376-48-9 ]
  • 33
  • [ 637-69-4 ]
  • [ 18640-74-9 ]
  • [ 1236376-49-0 ]
  • 34
  • [ 405-99-2 ]
  • [ 18640-74-9 ]
  • 5-[(E)-4-fluorostyryl]-2-isobutylthiazole [ No CAS ]
  • 35
  • [ 2680-03-7 ]
  • [ 18640-74-9 ]
  • [ 1236376-47-8 ]
  • 36
  • [ 1663-39-4 ]
  • [ 18640-74-9 ]
  • [ 1236376-44-5 ]
  • 37
  • [ 141-32-2 ]
  • [ 18640-74-9 ]
  • C14H21NO2S [ No CAS ]
  • 38
  • [ 937-41-7 ]
  • [ 18640-74-9 ]
  • [ 1236376-45-6 ]
  • 39
  • [ 18640-74-9 ]
  • [ 97-88-1 ]
  • [ 1236376-53-6 ]
  • [ 1236376-51-4 ]
  • 40
  • [ 13329-40-3 ]
  • [ 18640-74-9 ]
  • [ 1255536-55-0 ]
  • 41
  • [ 1461-22-9 ]
  • [ 18640-74-9 ]
  • [ 446286-02-8 ]
YieldReaction ConditionsOperation in experiment
To a solution of <strong>[18640-74-9]2-isobutylthiazole</strong> (5.0 mL, 35.4 mmol) in THF (100 mL) at -78 C. was added a 2 M solution of LDA (21.0 mL, 42.2 mmol) dropwise over 10 min. After 1 h at this temperature, Bu3SnCl (11.5 mL, 42.4 mmol) was added dropwise. The mixture was allowed to gradually warm to rt over about 3 h whereupon the mixture was quenched with sat. aq. NH4Cl (15 mL) and diluted with Et2O (70 mL). The layers were separated and the aqueous layer was extracted with Et2O (2×70 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated under reduced pressure to afford the desired compound as an orange/brown oil. MS:=430.4 The material was taken on crude to the next transformation without purification.
  • 42
  • [ 18640-74-9 ]
  • [ 108-90-7 ]
  • [ 600732-10-3 ]
  • 43
  • [ 1551-27-5 ]
  • [ 402-43-7 ]
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  • [ 1127217-52-0 ]
  • [ 1259389-29-1 ]
  • 44
  • [ 98-01-1 ]
  • [ 402-43-7 ]
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  • [ 1259389-29-1 ]
  • [ 55377-77-0 ]
  • 45
  • [ 768-18-3 ]
  • [ 402-43-7 ]
  • [ 18640-74-9 ]
  • [ 1259389-29-1 ]
  • [ 1259389-30-4 ]
  • 46
  • [ 1826-11-5 ]
  • [ 402-43-7 ]
  • [ 18640-74-9 ]
  • [ 1259389-29-1 ]
  • 2-phenyl-5-(4-(trifluoromethyl)phenyl)thiazole [ No CAS ]
  • 47
  • [ 4368-68-7 ]
  • [ 402-43-7 ]
  • [ 18640-74-9 ]
  • 1-benzyl-5-[4-(trifluoromethyl)phenyl]-1H-1,2,3-triazole [ No CAS ]
  • [ 1259389-29-1 ]
  • 48
  • [ 15764-47-3 ]
  • [ 402-43-7 ]
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  • [ 909104-05-8 ]
  • [ 1259389-29-1 ]
  • 50
  • [ 402-43-7 ]
  • [ 18640-74-9 ]
  • [ 95-15-8 ]
  • 2-[4-(trifluoromethyl)phenyl]-benzo[b]thiophene [ No CAS ]
  • [ 1259389-29-1 ]
  • 51
  • [ 603-76-9 ]
  • [ 18640-74-9 ]
  • [ 1312440-21-3 ]
  • 52
  • [ 1204606-34-7 ]
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  • [ 1339939-79-5 ]
  • 53
  • [ 18640-74-9 ]
  • [ 169330-64-7 ]
  • [ 1339939-70-6 ]
  • 54
  • [ 1334167-58-6 ]
  • [ 18640-74-9 ]
  • [ 1334166-15-2 ]
YieldReaction ConditionsOperation in experiment
29% Palladium (II) acetate (0.011 g, 0.05 mmol) and tert-butyldicyclohexylphosphine (0.027 ml, 0.1 mmol) were added to a stirred solution of intermediate 33 (0.3 g, 1.01 mmol), <strong>[18640-74-9]2-isobutylthiazole</strong> (0.142 g, 1.01 mmol) and potassium phosphate (0.428 g, 2.01 mmol) in N-methylpyrrolidine (4 ml). The mixture was stirred at RT for 15 min. under nitrogen and then at 125 C for 18 h. The mixture was diluted with Et20 and extracted with a 1% solution of potassium hydroxide. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 40/60). The desired fractions were collected and evaporated in vacuo and the crude product purified by RP HPLC (0.1% solution of ammonium formate/ammonium hydroxide buffer pH 9 in ACN 80/20 to 0/100). The desired fractions were collected and evaporated in vacuo to yield compound 42 (0.104 g, 29%>) as a yellow solid.
29% With potassium phosphate;dicyclohexyl-tert-butylphosphine; palladium diacetate; In 1-Methylpyrrolidine; at 125℃; for 18h;Inert atmosphere; Example B42 3-(2-Isobutyl-thiazol-5-yl)-2-methyl-8-morpholin-4-yl-imidazo[1,2-c]pyrazine Palladium (II) acetate (0.011 g, 0.05 mmol) and tert-butyldicyclohexylphosphine (0.027 ml, 0.1 mmol) were added to a stirred solution of intermediate 33 (0.3 g, 1.01 mmol), <strong>[18640-74-9]2-isobutylthiazole</strong> (0.142 g, 1.01 mmol) and potassium phosphate (0.428 g, 2.01 mmol) in N-methylpyrrolidine (4 ml). The mixture was stirred at RT for 15 min. under nitrogen and then at 125 C. for 18 h. The mixture was diluted with Et2O and extracted with a 1% solution of potassium hydroxide. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 40/60). The desired fractions were collected and evaporated in vacuo and the crude product purified by RP HPLC (0.1% solution of ammonium formate/ammonium hydroxide buffer pH 9 in ACN 80/20 to 0/100). The desired fractions were collected and evaporated in vacuo to yield compound 42 (0.104 g, 29%) as a yellow solid.
  • 55
  • [ 38940-62-4 ]
  • [ 18640-74-9 ]
  • [ 1393709-27-7 ]
YieldReaction ConditionsOperation in experiment
94% With PdCl(C3H5)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 150℃; for 20h;Inert atmosphere; In a typical experiment, the bromopyridine (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb) (6.8 mg, 0.01 mmol), were dissolved in DMAc (4 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C or 150 C (see schemes) for 20 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.
  • 56
  • [ 35590-37-5 ]
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  • [ 1393709-36-8 ]
YieldReaction ConditionsOperation in experiment
92% With PdCl(C3H5)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 150℃; for 20h;Inert atmosphere; In a typical experiment, the bromopyridine (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb) (6.8 mg, 0.01 mmol), were dissolved in DMAc (4 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C or 150 C (see schemes) for 20 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.
  • 57
  • [ 13472-85-0 ]
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  • [ 1393709-56-2 ]
YieldReaction ConditionsOperation in experiment
68% With PdCl(C3H5)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 150℃; for 20h;Inert atmosphere; In a typical experiment, the bromopyridine (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb) (6.8 mg, 0.01 mmol), were dissolved in DMAc (4 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C or 150 C (see schemes) for 20 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.
  • 58
  • [ 29681-44-5 ]
  • [ 18640-74-9 ]
  • [ 1393709-26-6 ]
YieldReaction ConditionsOperation in experiment
18% With PdCl(C3H5)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 100℃; for 20h;Inert atmosphere; In a typical experiment, the bromopyridine (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb) (6.8 mg, 0.01 mmol), were dissolved in DMAc (4 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C or 150 C (see schemes) for 20 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.
  • 59
  • [ 766-11-0 ]
  • [ 18640-74-9 ]
  • [ 1393709-53-9 ]
YieldReaction ConditionsOperation in experiment
77% With PdCl(C3H5)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 150℃; for 20h;Inert atmosphere; In a typical experiment, the bromopyridine (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb) (6.8 mg, 0.01 mmol), were dissolved in DMAc (4 mL) under an argon atmosphere. The reaction mixture was stirred at 100 C or 150 C (see schemes) for 20 h. After evaporation of the solvent, the product was purified by silica gel column chromatography.
  • 60
  • [ 29632-74-4 ]
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  • [ 106-40-1 ]
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  • 69
  • [ 5332-24-1 ]
  • [ 18640-74-9 ]
  • 3-(2-isobutylthiazol-5-yl)quinoline [ No CAS ]
  • 70
  • [ 6952-59-6 ]
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  • [ 1404074-50-5 ]
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  • 77
  • [ 73583-37-6 ]
  • [ 18640-74-9 ]
  • 2-chloro-4-(2-isobutylthiazol-5-yl)pyridine [ No CAS ]
  • 78
  • [ 18640-74-9 ]
  • 4-(2-isobutylthiazol-5-yl)-2-phenylpyridine [ No CAS ]
  • 79
  • [ 18640-74-9 ]
  • 1-{2-[4-(2-isobutylthiazol-5-yl)pyridin-2-yl]phenyl}ethanone [ No CAS ]
  • 80
  • [ 18640-74-9 ]
  • 3-(2-isobutylthiazol-5-yl)-2-phenylpyridine [ No CAS ]
  • 81
  • [ 18640-74-9 ]
  • 3-(2-isobutylthiazol-5-yl)-2-(4-trifluoromethylphenyl)pyridine [ No CAS ]
  • 82
  • [ 18640-74-9 ]
  • 1-{4-[3-(2-isobutylthiazol-5-yl)pyridin-2-yl]phenyl}ethanone [ No CAS ]
  • 83
  • [ 18640-74-9 ]
  • 3-(2-isobutylthiazol-5-yl)-2-(3-nitrophenyl)pyridine [ No CAS ]
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