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Structure of 81569-25-7

Chemical Structure| 81569-25-7

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Product Details of [ 81569-25-7 ]

CAS No. :81569-25-7
Formula : C8H12N2O2S
M.W : 200.26
SMILES Code : COC(=O)C1=C(SC(N)=N1)C(C)C
MDL No. :MFCD01924792
InChI Key :YEJDFNBFDCUMAG-UHFFFAOYSA-N
Pubchem ID :737584

Safety of [ 81569-25-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
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

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   1~3

  • 1
  • [ 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).
  • 2
  • [ 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.
  • 3
  • [ 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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