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[ CAS No. 81569-25-7 ] {[proInfo.proName]}

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Product Details of [ 81569-25-7 ]

CAS No. :81569-25-7 MDL No. :MFCD01924792
Formula : C8H12N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :YEJDFNBFDCUMAG-UHFFFAOYSA-N
M.W : 200.26 Pubchem ID :737584
Synonyms :

Calculated chemistry of [ 81569-25-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.38
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) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 0.53
Log Po/w (SILICOS-IT) : 2.12
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.803 mg/ml ; 0.00401 mol/l
Class : Soluble
Log S (Ali) : -3.54
Solubility : 0.0581 mg/ml ; 0.00029 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.84
Solubility : 2.89 mg/ml ; 0.0145 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 81569-25-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501 UN#:
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 81569-25-7 ]

* 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 [ 81569-25-7 ]

[ 81569-25-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 81569-25-7 ]
  • [ 81569-27-9 ]
YieldReaction ConditionsOperation in experiment
1.45 g With sulfuric acid; copper(II) sulfate; sodium chloride; sodium nitrite In water 0 deg C, 30 min -> 20 deg C, 30 min;
  • 2
  • [ 81569-25-7 ]
  • [ 81569-28-0 ]
YieldReaction ConditionsOperation in experiment
60% With copper(I) bromide; isopentyl nitrite In acetonitrile at 80℃; for 3h; 42A Methyl 2-bromo-5-isopropylthiazole-4-carboxylate To a solution of methyl 2-amino-5-isopropylthiazole-4-carboxylate (1.000 g, 4.99 mmol) in CH3CN (10 mL) was added isopentyl nitrite (1.073 mL, 7.99 mmol) followed by copper(I) bromide (1.433 g, 9.99 mmol) and the resulting mixture was heated at 80 °C for 3 h. The reaction mixture was then concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was separated, filtered through a CELITE pad and concentrated. The residue was purified on the ISCO using a REDISEP 24 g column (0 to 40% EtOAc-hexanes) to give the desired product as a light red oil (0.787 g, 60%). LCMS (APCI): calcd for C8H11BrNO2S [M+H]+ m/z 263.962, found 264.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 4.17 (dt, J= 13.7, 6.8 Hz, 1H), 3.94 (s, 3H), 1.35 (s, 3H), 1.33 (s, 3H).
1.5 g With sulfuric acid; copper(II) sulfate; sodium bromide; sodium nitrite In water
  • 3
  • [ 81569-25-7 ]
  • [ 864437-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaNO2; H3PO2 2: aq. LiOH / methanol
Multi-step reaction with 2 steps 1.1: hypophosphorous acid; sodium nitrite / -5 - 0 °C 2.1: sodium hydroxide / methanol / 18 h / 20 °C 2.2: pH 2
  • 4
  • [ 53308-95-5 ]
  • [ 81569-25-7 ]
  • [ 649737-03-1 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 16h; A solution of 2.3 g of methyl 2-amino-5-(1-methylethyl)thiazole-4-carboxylate, obtained in Example 1, in 100 ml of dimethylformamide at 0° C. is admixed with 1.22 g of N-methylmorpholine, 6.34 g of PyBOP and then 2.65 g of (S)-Boc-norvaline. The reaction medium is allowed to return to ambient temperature and then is stirred for 16 h. Following evaporation, the residue is taken up in ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution, twice with water, once with a 1H aqueous solution of potassium hydrogen sulfate and then with saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate and then concentrated. The residue is chromatographed on a silica gel column, eluding with a 3:7(v/v) ethyl acetate/petroleum ether mixture. This gives 3.5 g of a white solid. NMR 300 MHz (CDC13) delta ppm: 0.97 (t, 3H); 1.37 (d, 6H); 1.45 (s, 9H); 1.67 (m, 2H); 1.90 (m, 2H); 3.90 (s, 3H); 4.10 (m, 1H); 4.38 (unresolved complex, 1H); 4.90 (unresolved complex, 1H). A solution of 3.3 g of the product obtained above in 60 ml of trifluoroacetic acid is stirred at ambient temperature for 30 min, followed by evaporation. The residue is taken up in ethyl acetate and washed twice with saturated aqueous sodium carbonate solution and then with saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate and then evaporated to give 2 g of a white solid. NMR 300 MHz (CDC13) delta ppm: 0.97 (t, 3H); 1.35 (d, 6H); 1.40 to 1.60 (m, 2H); 1.80 (m, 2H); 3.60 (m, 1H); 3.97 (s, 3H); 4.12 (m, 1H).
  • 5
  • [ 81569-25-7 ]
  • [ 51293-47-1 ]
  • [ 649739-06-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 18h; A solution of 2.00 g of methyl 2-amino-5-(1-methylethyl)thiazole-4-carboxylate, obtained in Example 1, in 100 ml of dimethylformamide at 0° C. is admixed with 1.01 g of N-methylmorpholine, 5.72 g of PyBOP and then 2.40 g of (S)-BOC-O-methylserine, dicyclohexylamine. The reaction is allowed to return to ambient temperature and the mixture is stirred for 18 h. The solvent is evaporated and the residue is taken up in ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution, once with water and once with a 1N aqueous solution of potassium hydrogen sulfate and then with saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a silica column, eluting with an 8:2 (v/v) petroleum ether/ethyl acetate mixture, to give 2.70 g of a white powder. LC/MS: MH+=402. NMR 300 MHz (CDC13): 1.33 (d, 6H); 1.48 (s, 9H); 3.32 (s, 3H); 3.33 and 3.99 (2m, 2H); 3.55 (m, 1H); 3.92 (s, 3H); 4.13 (m, 1H); 4.5 (broad s 1H); 5.40 (d, 1H). A solution of 4.30 g of the product obtained in the manner described above, in 60 ml of trifluoroacetic acid, is stirred at ambient temperature for 30 min, and then the solution is evaporated. The residue is taken up in ethyl acetate and washed twice with saturated aqueous sodium carbonate solution and then with saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate and then evaporated to give 0.50 g of a white solid, which is used without purification in the following step.
  • 6
  • [ 207981-46-2 ]
  • [ 81569-25-7 ]
  • [ 1231955-39-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; Example 34; methyl (2Z)-3 -butyl-2- { [2- [(tert-butylamino)oxy ]-5 -(trifluoromethyl)benzoyllimino I -5 - isopropyl-2,3-dihydro- 1 ,3-thiazole-4-carboxylate; Example 34A; methyl 5-isopropyl-2-[2-fluoro-5-(trifluoromethyl)benzoyllamino|-l,3-thiazole-4- carboxylate; A mixture of commercially available methyl 2-amino-5-isopropylthiazole-4- carboxylate (1 g, 4.99 mmol) and <strong>[207981-46-2]2-fluoro-5-(trifluoromethyl)benzoyl chloride</strong> (1.31 g, 5 mmol) in anhydrous CH2Cl2 (25 mL) was treated dropwise at 0 0C with triethylamine (0.84 mL, 6 mmol). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with hexanes-EtOAc (1 : 1) to afford 1.8 g of the title compound. MS (DCI/NH3) m/z 391 (M+H)+.
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