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Chemical Structure| 1207457-37-1 Chemical Structure| 1207457-37-1

Structure of 1207457-37-1

Chemical Structure| 1207457-37-1

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Product Details of [ 1207457-37-1 ]

CAS No. :1207457-37-1
Formula : C12H9N3O3S
M.W : 275.28
SMILES Code : O=C(O)CCC(NC1=CC=C2N=C(C#N)SC2=C1)=O

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Application In Synthesis of [ 1207457-37-1 ]

* 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 [ 1207457-37-1 ]

[ 1207457-37-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 108-30-5 ]
  • [ 7724-12-1 ]
  • [ 1207457-37-1 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran; at 110℃; for 1.5h;Microwave irradiation; 4-((2-cyanobenzo[d]thiazol-6-yl)amino)-4-oxobutanoic acid (1). 6- aminobenzo[d]thiazole-2-carbonitrile (2.0 g, 11.4 mmol), succinic anhydride (1.3 g, 13 mmol) and THF (15 mL) were placed in a 25 mL vessel and heated in a microwave synthesizer for 90 minutes at 110°C. Upon cooling, the reaction mixture was triturated with Et20 and filtered, dried and evaporated to give 3.1 g of the product as a light yellow solid (99percent). IH-NMR (d6-DMSO, 300 MHz): delta 12.15 (s, 1H), 10.45 (s, 1H), 8.71 (s, 1H), 8.16 (d, 1H, J = 8.2 Hz), 7.70 (d, 1H, J= 8.2 Hz), 2.62 (m, 2H), 2.55 (m, 2H). ESI-MS: Calc. C12H10N3O3S +: m/z 276.3; found m/z 276. tert-butyl (18-((2-cyanobenzo [d] thiazol-6-yl)amino)- 15,18-dioxo-4,7, 10-trioxa-14- azaoctadecyl)carbamate (2). Compound 1 (4.93g, 17.9 mmol), tert-butyl (3-(2-(2-(3- aminopropoxy)ethoxy)ethoxy)propyl)carbamate (7.40 g, 23.1 mmol) and DCM:DMF (10: 1, 100 mL) were stirred together in a 250 mL round bottomed flask at room temperature. ED AC (4.0 g, 20.9 mmol) was added and the reaction was stirred for 20h. The solvent was evaporated and purified by normal phase chromatography with DCM/MeOH as solvent to give 6.62 g of a white solid (64percent). IH-NMR (d3-ACN, 300 MHz): delta 9.21 (s, NH), 8.62 (d, 1H, J = 2.0 Hz), 8.09 (d, 1H, J = 8.4 Hz), 7.63 (d, 1H, J = 8.4 Hz), 6.65 (bs, NH), 5.40 (bs, NH), 3.5 (m, 12 H), 3.28 (m, 2H), 3.06 (m, 2H), 2.65 (m, 2H), 2.51 (m, 2H), 2.70 (m, 4H), 1.40 (s, 9H). ESI-MS: Calc. C27H40N5O7S +: m/z 578.7; found m/z 578.4. Nl-(3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)-N4-(2-cyanobenzo[d]thiazol-6- yl)succinamide hydrochloride (3). Compound 2 (6.62 g, 11.5 mmol) was stirred in a 500 mL round bottomed flask with DCM (200 mL) and triisopropylsilane (1 mL). A 4.0 M solution of HCl in dioxane (30 mL, 120 mmol) was added and stirred at room temperature for 3h. The solvent was evaporated to give 6.4 g of a yellow hygroscopic solid (98percent). 1H-NMR (d6-DMSO, 300 MHz): delta 10.62 (s, 1H), 8.74 (d, 1H, J = 2.0 Hz), 8.15 (d, 1H, J = 8.4 Hz), 7.77 (d, 1H, J = 8.4 Hz), 3.4 (m, 16 H), 3.28 (m, 2H), 3.08 (m, 2H), 2.80(m, 2H), 2.61 (m, 2H), 2.41 (m, 2H), 1.80, (m, 2H), 1.60 (m, 2H). ESI-MS: Calc. C22H32N505S +: m/z 478.59; found m/z 478.2. Immobilized cyanobenzothiazole-magnetic cellulose (4). Carboxymethyl magnetic cellulose (7.24g, 30-50 muiotaeta, Iontosorb MG CM) was taken up in a 250 mL round bottomed flask with compound 3 (800 mg, 1.53 mmol) in DMF (100 mL). ED AC (387 mg, 2.01 mmol) was added, and the reaction was stirred for 20h at room temperature. The particles were filtered on a frit and rinsed first with DMF (200 mL) then 25percent EtOH (300 mL) and stored as a 50percent> suspension at 4°C.
 

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