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Chemical Structure| 368869-97-0 Chemical Structure| 368869-97-0

Structure of 368869-97-0

Chemical Structure| 368869-97-0

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Product Details of [ 368869-97-0 ]

CAS No. :368869-97-0
Formula : C12H9NO3S
M.W : 247.27
SMILES Code : O=C(C1=CSC(C2=CC=C(OCC3)C3=C2)=N1)O
MDL No. :MFCD01313485

Safety of [ 368869-97-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 368869-97-0 ]

* 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 [ 368869-97-0 ]

[ 368869-97-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 368869-97-0 ]
  • [ 170017-74-0 ]
  • [ 1029431-78-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 80℃; for 15h; Example 19Preparation of Compound 16 To a solution of 2-(2,3-Dihydro-benzofuran-5-yl)-thiazole-4-carboxylic acid (0.10 mmol, 25 mg), λ/,λ/-diisopropylethylamine (0.50 mmol, 87 μL) and HATU (0.10 mmol, 38 mg) in DMF (2 mL) was added 4-(2-amino-phenyl)-piperazine-1-carboxylic acid te/t-butyl ester (0.1 mmol). The reaction mixture heated to 800C and allowed to stir at this temperature for about 15 hours, then concentrated in vacuo and the resulting residue was treated with TFA (0.5 mL) with stirring for 10 minutes. The TFA solution was then concentrated in vacuo and the resulting residue was dissolved in DMSO/ACN (3:1 ) and purified using reverse phase HPLC to provide Compound 16 as an ammonium salt.
  • 2
  • [ 368869-97-0 ]
  • [ 6142-15-0 ]
  • 2-(2,3-dihydro-1-benzofuran-5-yl)-N-(4-methyl-1,3-thiazol-2-yl)-1,3-thiazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With pyridine; at 100℃; for 5h; 2-(2,3-Dmydro-l-beiizofuran-5-yI)-/V-(4-inethyl-l,3-thiazol-2-yl)-l}3-thia2ole-4- carboxamide 72) To a mixture of 2-(2,3-dihy lro-l-benzofuran-5-yl)-l ,3-thiazok-4-carboxylic acid (80 mg, 0,32 mmol), 4-m ethyl thiazol-2-amine hydrochloride (49 mg, 0.32 mmol) and HBTU (120 mg, 0.32 mmol) under stirring and heating at 100 C, 1 ml of dry pyridine was added. The mixture was heated at 100 C for 5 h, pyridine was evaporated, and the residue was diluted with an aqueous Na2C03 solution. The resulting precipitate was filtered off and purified by flash column chromatography on silica gel (EtOAc as eluent). The product was obtained as a pale yellow solid (60 mg, 0.17 mmol, 55 % yield). FontWeight="Bold" FontSize="10" H NMR (DMS0-< CC14) delta ppm 2.34 (s, 3 H), 3.30 (t, J = 8.6 Hz, 2 H), 4.64 (t, J = 8.6 Hz, 2 H), 6.70 (s, 1 H), 6.81 (d, J = 8.6 Hz, 1 H), - I l l - 7.84 (dd, J = 8.6, 2.0 Hz, 1 H), 8.03 (d, J = 1.2 Hz, 1 H), 8.38 (s, 1 H), 11.74 (bs, 1 H). M.p.: 136-138 C. LC MS [M+H]+: 343.8.
  • 3
  • [ 368869-97-0 ]
  • [ 63655-40-3 ]
  • N-(5-cyano-1H-benzo[d]imidazol-2-yl)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; AL(5-Cyano-lH-benzo[^imidazol-2-yl)-2-(2,3-dihydrobenzofuraii~5-yl)thiazole-4- To a solution of 2-(2,3-dihydro-l-berizofuran-5-yl)-l 3-thiazole-4-carboxylic acid (123 nag, 0.50 mmol) in 2 ml N,N-dimethylformamide, were added 2-amino~lH-benzo[c jimidazole-5- carbonitrile (130 mg, 0.54 mmol), 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HBTU) (188 mg, 0.5 mmol), 4-dimethylaininopyridine (6 mg, 0.05 mmol) and NN-diisopropylethylamine (0.22 ml, 1.24 mmol). The reaction mixture was stirred overnight at room temperature. It was poured into ice water. The foraied precipitate was filtered off and dried. The product was obtained as a light yellow solid (154 mg, 0.40 mmol, 79 % yield). FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-<) delta ppm 3.29 (t, J=8.75 Hz, 2 H), 4.65 (t, J=8.75 Hz, 2 H), 6.91 (d, J=8.34 Hz, 1 H), 7.54 (dd, J=8.25 Hz, j=1.32 Hz, 1 H), 7.67 (d, j=8.28 Hz, 1 H), 7.92 (d, J-1.92 Hz, 1 H), 7.95 (bs, 1 H), 8.13 (bs, 1 H), 8.58 (s, 1 H), 11.84 (bs, 1 H), 12.69 (bs, 1 H). LC/MS [M+H]+: 387.8
  • 4
  • [ 368869-97-0 ]
  • [ 42182-27-4 ]
  • N-(4-cyanopyridin-2-yl)-2-(2,3-dihydrobenzofuran-5-yl)thiazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1% With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; -(4-Cyanopyridin-2-yl)-2-(2,3-dihydrobenzofuraii-5-yl)thiazole-4-carboxamide (18) To a solution of 2-(2,3-dihydro-l-benzofuran-5-yl)-l,3-thiazole-4-carboxylic acid (1.00 mg, 0.40 mmol) in 4 ml NN-dimethylformamide was added 2-Amino-4-cyanopyridine (53 mg, 0.44 mmol). Then 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluiOnium hexaf oro- phosphate (HBTU) (153 mg, 0.40 mmol), 4-dimethylaminopyridine (5 mg, 0.04 mmol) and N,N-diisopropylethylamine (0.18 ml, 1.01 mmol) were added. The reaction mixture was stirred overnight at room temperature. Additional 4-dimethylaminopyridine (5 mg, 0.04 mmol) was added and the mixture was stirred at room temperature for 5 days. Additional NN-diisopropylethylamine (0.18 ml, 1.01 mmol) and 2-(lH-benzotriazole-l-yl)-l, 1,3,3- tetramethyluronium hexafluorophosphate (HBTU) (77 mg, 0.20 mmol) were added and the mixture was stirred at room temperature for 18 h. The mixture was diluted with EtOAc and the biphasic mixture was separated. The organic layer was washed three times with an aqueous 5percent NaHC( solution. The organic layer was dried over MgSC>4 and concentrated in vacuo. The crude product was purified by preparative TLC (PLC silica gel 60 F254, 2 mm, eluent: DCM:MeOH 95:5). The product was obtained as a white solid (1 mg, 0.003 mmol, 1 percent yield). H NMR (400 MHz, DMSO-<) delta ppm 3.25-3.34 (m, 2 H), 4.64 (t, J=8.78 Hz, 2 H), 6.91 (d, J=8.28 Hz, 1 H), 7.66 (dd, J=5.04 Hz, J=1.41 Hz, 1 H), 7.87 (dd, J=8.34 Hz, J=2.01 Hz, 1 H), 8.04 (d, J-1.53 Hz, 1 H), 8.51 (dd, J=l,35 Hz, J-0.93 Hz, 1 H), 8.53 (s, 1 H), 8.67 (dd, J-5.06 Hz, 7=0.90 Hz, 1 H), 10.49 (bs, 1 H). LC/MS [M+H]+: 349.0
  • 5
  • [ 63666-11-5 ]
  • [ 368869-97-0 ]
  • ethyl 5-(2-(2,3-dihydrobenzofuran-5-yl)thiazole-4-carboxamido)-4H-1,2,4-triazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With pyridine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; at 80℃; for 15.0h; Method A. To a suspension of 2-(2,3-dihydro-l -benzofuran-5-yl)-l,3-thiazole-4-carboxylic acid (381 mg, 1.54 mmol) and ethyl 5-amino-l,2,4-triazole-3-carboxylate (219 mg, 1.54 mmol) in 5.4 ml dry pyridine at boiling 2-(lH-benzotriazole-l-yl)-l,l53,3-tetramethyluronium hexafluorophosphate (HBTU) (643 mg, 1.70 mmol) was added in portions while solid dissolves gradually; clear solution forms 5 minutes after all 2-(lH-benzotriazole-l-yl)~l, 1,3,3- tetramethyluronium hexafluorophosphate (HBTU) was added. The solution war kept at stirring at 80 C during 15 h. Pyridine was evaporated to dryness, residue was washed with water, an aqueous NaHC03 solution, water, diluted aqueous AcOH and again water. The residue was dissolved in hot N,N-dimethylfonriamide, filtered, filtrate was evaporated to dryness, the residue was treated with boiling ethanol, cooled and filtered off. The procedure was repeated twice after which the residue was washed with ether and dried to give (339 mg, 0.88 mmol, 57 %) pure product. lE NMR (400 MHz, DMSO-c) delta ppm 14.16 (s, 1H, NH), 11.95 (s, 1H, NH), 8.46 (s, 1H, CH-thiazole), 8.08 (s, 1H, CH-Ar), 7.88 (d, J = 8.2 Hz, 1H, CH-Ar), 6.84 (d, J = 8.3 Hz, 1H, CH-Ar), 4.65 (t, J = 8.7 Hz, 2H, OCH2CH2), 4.34 (q, J = 7.0 Hz, 2H, OCH2CH3), 3.30 (t, J = 8.7 Hz, 1H, OCH2CH2), 1.37 (t, J = 7.1 Hz, 3H, OCCH3). LC/MS [M+H]+: 386.0
 

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