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[ CAS No. 57626-37-6 ]

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2D
Chemical Structure| 57626-37-6
Chemical Structure| 57626-37-6
Structure of 57626-37-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 57626-37-6 ]

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Related Doc. of [ 57626-37-6 ]

SDS

Product Details of [ 57626-37-6 ]

CAS No. :57626-37-6MDL No. :MFCD01060560
Formula :C9H10N2O2SBoiling Point :-
Linear Structure Formula :-InChI Key :NSUFDDBQLKSSIN-UHFFFAOYSA-N
M.W :210.25Pubchem ID :671011
Synonyms :

Computed Properties of [ 57626-37-6 ]

TPSA : 71.8 H-Bond Acceptor Count : 4
XLogP3 : 2.8 H-Bond Donor Count : 0
SP3 : 0.33 Rotatable Bond Count : 3

Safety of [ 57626-37-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57626-37-6 ]

  • Upstream synthesis route of [ 57626-37-6 ]
  • Downstream synthetic route of [ 57626-37-6 ]

[ 57626-37-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 96-50-4 ]
  • [ 609-15-4 ]
  • [ 57626-37-6 ]
YieldReaction ConditionsOperation in experiment
82% at 90℃; for 6.00 h; 2-Aminothiazole (3.00 g, 29.99 mmol) and 2-chloroethylacetoacetate(4.96 mL, 35.99 mmol) were taken in 1,2-dimethoxyethane(30 mL) and heated at 90 C for 6 h. The reactionmixture was concentrated under reduced pressure, diluted withEtOAc (80 mL), washed the organic layer with H2O (3 30 mL).The separated organic layer was dried over anhyd Na2SO4 and concentratedunder vacuo to get crude compound. The crude compoundwas purified by column chromatography using 20percent EtOAcin Hexanes as eluent to get ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate (2a) (5.20 g, 82percent) as an Off-white solid. ESIMSshowed 211 [M+H]+ and carried to next step.
26% at 80℃; for 24.00 h; [001195] (i) Production of ethyl 6-methylimidazo[2,l-b][l,3]thiazole-5-carboxylate[001196] A mixture of l,3-thiazol-2-amine (10 g, 100 mmol), ethyl 2-chloro-3-oxobutanoate (16 g, 100 mmol) and ethanol (100 mL) was stirred at 800C for 1 day. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80- 50/50) and washed with diisopropyl ether to give the title compound (5.5 g, 26percent) as a colorless solid.[001197] 1H-NMR (DMSO-d6, 300 MHz) 5 1.34 (3H, t, J = 7.2 Hz), 2.51 (3H, s), 4.33 (2H, q, J = 7.2Hz), 7.44 (IH, d, J = 4.3 Hz), 8.08 (IH, d, J = 4.3 Hz).
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1298 - 1307
[2] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 981 - 983
[3] Patent: WO2010/90716, 2010, A1. Location in patent: Page/Page column 328
[4] Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 533 - 545
[5] Archiv der Pharmazie, 1976, vol. 309, # 12, p. 959 - 965
[6] Patent: US2010/152192, 2010, A1. Location in patent: Page/Page column 10
[7] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 24, p. 5916 - 5919
[8] Patent: WO2010/70452, 2010, A1. Location in patent: Page/Page column 23
  • 2
  • [ 96-50-4 ]
  • [ 84911-18-2 ]
  • [ 57626-37-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 1975, vol. 10, # 1, p. 59 - 64
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 2029 - 2032
[3] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3662 - 3666
  • 3
  • [ 84911-18-2 ]
  • [ 96-50-4 ]
  • [ 57626-37-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 1982, vol. 17, # 3, p. 271 - 274
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