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Chemical Structure| 302964-06-3 Chemical Structure| 302964-06-3

Structure of 302964-06-3

Chemical Structure| 302964-06-3

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Product Details of [ 302964-06-3 ]

CAS No. :302964-06-3
Formula : C16H18ClN3O3S
M.W : 367.85
SMILES Code : O=C(OC(C)(C)C)NC1=NC=C(C(NC2=C(C)C=CC=C2Cl)=O)S1
MDL No. :MFCD34181790
InChI Key :QUVXAYSRBLGINB-UHFFFAOYSA-N
Pubchem ID :18184791

Safety of [ 302964-06-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 302964-06-3 ]

* 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 [ 302964-06-3 ]

[ 302964-06-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 87-63-8 ]
  • [ 302964-20-1 ]
  • [ 302964-06-3 ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30℃; for 25.5h; Into a clean and dry 3L 4-neck round bottom flask connected to a mechanical stirrer,condenser and thermometer socket is charged with <strong>[302964-20-1]2-tert-butoxycarbonylamino-thiazole-5-carboxylic acid chloride</strong> (4) crude (27.5 g) and dichloromethane (750 mL) under stirring. Cooled the reaction mass to 0-5 C and add 2-chloro-6-methylaniline (22.2 g) to the reaction mass at 0-5 C within 30-45 min period. Added DiPEA to the reaction mass at 0-5 C in 30-45 min period, raised the reaction mass temperature to 25-30 C and stirred the reaction mass at 25-30 C for 24 h. After TLC compliance distilled-off the solvent completely under plant vacuum at the temperature not crossing 50 C and Charge 2 N HCl (250 mL) to the reaction mass, Stirred for 15-30 min. Transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. The wet cake is washed with 500mL of water and dried the above-wet material in the dryer at temperature 60-65 C for 10-12 h. Purification: Into a clean and dry 3.0 L 4-neck round bottom flask connected to a mechanical stirrer, condenser, thermometer socket is charging with 2-tert-butoxy-carbonyl-amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide crude, methanol and isopropyl ether under stirring at 25- 30 C. Raised the reaction mass temperature to 60-65 C and stirred the reaction mass at 60-65 C for 45-60 min. Cooled the reaction mass temperature to 25-30 C and transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. Washed the wet cake with 20.0 mL of methanol and dried the wet material in dryer at 60-65 C for 4-6 h to furnish 16.0 g of the title compound with purity above 95 %. Cream colour solid; Elemental analysis C16H18N3O3SClcalcd (found) %: C 52.24 (52.12), H 4.93 (5.05), N 11.42 (11.31),O 13.05 (13.25), S 8.72 (8.83). IR (KBr, numax, cm-1): 3423.42-3276.87, 3162.67, 2928.46, 1724.90, 1632.68-1566, 1522.80,775.21; 1H NMR (400 MHz, DMSO-d6): delta1.504 (s, 9H, -3CH3),2.225 (s, 3H, -CH3), 7.262-7.301 (t, 2H, ArH), 7.389-7.412(m, 1H, ArH), 8.204 (s, 1H, ArH), 10.017 (s, 1H, -NH), 11.847(s, 1H, -NH); 13C NMR (100 MHz, DMSO-d6): delta163.220, 159.74,152.91, 141.27, 139.02, 133.31, 132.57, 129.34, 128.64, 127.28,126.62, 82.33, 28.06, 18.45; ESI-MS (m/z): 368.21 (M+1),370.18 (M+3)
With N-ethyl-N,N-diisopropylamine; In dichloromethane; [00106] Compound 8 was made using by adapfing the synthesisdsdosed n J.Med.Chem. 2006, 6819. Synthesis of amde 5 was accomphshedn two steps, starting from compound 1. Compound I was converted to acidchorde 2 using oxay chorde n dchoromethane (DCM). Formafion of theacd chorde was confirmed by quenching an aquot n methano (MeOH);LCMS anayss ndcated the presence of the corresponding methy? ester 3 n>90%. Add Won of 2 to a mixture of excess anWne 4 and dsopropy ethyamne(DPEA) gave good conversion to amine 5. After fHtehng the sohds off thisafforded 1.15 g (40%) amde 5 n high purIty. Remova of the Boc-group using tr[fluoroacefic acid (TFA) gave good conversion to amine 6. Amine 6 was converted to compound 8 n the presence of compound 7 and sodium t-butoxde (NaOBu-t).
16.0 g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30℃; Into a clean and dry 3.0.L 4-neck RB flask charged 2- tert-Butoxycarbonylamino- thiazole-5-carboxylic acid chloride crude (28 gm) and methylene chloride (750 (0089) ml) under stirring, cooled the reaction mass to temperature to 0-5C. Added 2- Chloro-6-methyl aniline (23gm) to the reaction mass at temperature 0- 5C within 30-45 min period. Diisopropyl ethylamine (55 gm) was added to the reaction mass at temperature 0-5 C in 30-45 min period, reaction mass temperature was raised to 25-30C and maintained for 24 hrs, after completion of the reaction, distilled off the solvent completely under plant vacuum at temperature not crossing 50C. (0090) charged 2 HC1 to the reaction mass and stirred for 15-30 min, transferred the (0091) reaction mass into a buchner funnel and flask kept under plant Vacuum. Wet cake was washed with 250.0 ml of water and suck dried thoroughly for 30-45 min, wet material was transferred into a clean and dry petridish. Dried the above wet (0092) material in drier at temperature 60-65 C forlO-12 hrs. (0093) Weight: 20gm f) purification of 2-tert-butoxy- carbonyl amino-N-(2-chloro-6- methylphenyl)-5-thiazolecarboxamide (0095) Into a clean and dry 3.0.L 4-neck RB flask charged 2-tert-butoxy- carbonyl (0096) amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide crude(20gm) , (0097) methanol (250ml, Lot-1) and (0098) Isopropyl ether(200ml) under stirring at temperature 25- 30C, reaction mass (0099) temperature was raised to 60-65C and maintained for 45-60 min. cooled the (0100) reaction mass temperature to 25-30C and transferred the reaction mass into a (0101) buchner funnel and flask kept under plant vacuum. Washed the wet cake with (0102) 20.0 ml of methanol (LOT-II)and suck dried for 10-15min, and dried the (0103) compound in drier at temperature 60-65 C for 4-6 hrs. (0104) Weight: 16.0 g
 

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