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Chemical Structure| 2016-42-4 Chemical Structure| 2016-42-4

Structure of 2016-42-4

Chemical Structure| 2016-42-4

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Product Details of [ 2016-42-4 ]

CAS No. :2016-42-4
Formula : C14H31N
M.W : 213.40
SMILES Code : NCCCCCCCCCCCCCC
MDL No. :MFCD00008157
InChI Key :PLZVEHJLHYMBBY-UHFFFAOYSA-N
Pubchem ID :16217

Safety of [ 2016-42-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H319-H372-H410
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330
Class:9
UN#:3077
Packing Group:

Application In Synthesis of [ 2016-42-4 ]

* 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 [ 2016-42-4 ]

[ 2016-42-4 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 2016-42-4 ]
  • [ 57-92-1 ]
  • (1<i>R</i>)-<i>N</i>,<i>N</i>'-dicarbamimidoyl-<i>O</i>4-[<i>O</i>2-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(tetradecylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine [ No CAS ]
  • 2
  • [ 2016-42-4 ]
  • [ 2488-17-7 ]
  • [ 485323-71-5 ]
  • 3
  • [ 2016-42-4 ]
  • [ 1709-71-3 ]
  • 2-methyl-acrylic acid 2-hydroxy-3-[3-({2-[2-hydroxy-3-(2-methyl-acryloyloxy)-propoxycarbonyl]-ethyl}-tetradecyl-amino)-propionyloxy]-propyl ester [ No CAS ]
  • 4
  • [ 207399-07-3 ]
  • [ 2016-42-4 ]
  • C50H74N3(1+)*I(1-) [ No CAS ]
  • 5
  • [ 2016-42-4 ]
  • [ 6914-79-0 ]
  • [ 1266666-36-7 ]
  • 6
  • [ 2016-42-4 ]
  • [ 6914-79-0 ]
  • [ 1266665-34-2 ]
  • 7
  • [ 2016-42-4 ]
  • [ 63547-24-0 ]
  • [ 1410075-16-9 ]
  • 8
  • [ 2016-42-4 ]
  • [ 3543-75-7 ]
  • [ 1609623-15-5 ]
YieldReaction ConditionsOperation in experiment
57.6% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 3.3 - 20℃; for 3h;Inert atmosphere; 4-{5-[Bis-(2-chloro-ethyl)-amino]-l-methyl-lH-benzoimidazol-2-yl}-N-tetradecyl-butyramide (<strong>[3543-75-7]bendamustine</strong> CM amide): A 250 niL three neck round bottom flask equipped with a stir bar, thermocouple, cooling bath, 60 mL pressure equalizing dropping funnel and nitrogen in/outlet was charged with 10.0 g (25.3 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 10.6 g (27.8 mmol) of HATU and 100 mL of Nu,Nu-dimethylfomramide (DMF). To this stirred yellow solution was added 4.41 mL (3.27 g, 25.3 mmol) of Nu,Nu-diisopropylethyelamine (DIPEA). An exotherm to 27.1C was noted and the solution became a darker yellow. The reaction was cooled to 3.3C where a solution of 6.2 mL (4.59 g, 35.5 mmol) of DIPEA, 5.75 gf (25.6 mmol) of tetradecyl amine in 40 mL of DMF was added drop-wise over 6 min at <10C. Once addition was complete the reaction became very thick and difficult to stir. It was transferred to a 500 mL three neck round bottom flask equipped with an overhead stirrer and thermocouple, then stirred at RT for three hours at which time an in process analysis indicated the reaction was complete. The batch was quenched onto 400 mL of DI water and extracted with ethyl acetate (2 X 300 mL). the organic phases were combined, washed with 10% sodium hydrogen phosphate (1 X 300 mL), 8% aqueous sodium bicarbonate (1 X 300 mL) and brine (1 X 300 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo. The residue was purified by chromatography using lOOg of silica gel 60, 230-400 mesh, eluting with 1% MeOH/MDC (2 L), 2.5 % MeOH/MDC (1L) and 5% MeOH/MDC (1L) collecting -100 mL fractions. The product containing fractions were combined and concentrated to dryness in vacuo to yield 7.86 g (14.6 mmol, 57.6%) of the desired product as a white solid with an HPLC purity of 97.3A%.1H NMR (400 MHz, DMSO-d6) delta 7.72 (s, b, 1H), 7.33 (d, J= 8.84 Hz, 1H), 6.91 (d, J= 2.22 Hz, 1H), 6.80 (dd, J= 2.36, 8.84 Hz), 3.71 (s, 8H), 3.70 (s, 3H), 3.01 (q, J= 6.8, 12.68, 2H), 2.79 (t, J = 7.44 Hz, 2H), 2.18 (t, J= 7.36 Hz, 2H), 1.97 (m, 2H), 1.36 (m, 2H), 1.28 (s, b, 22), 0.84 (t, J = 7.04 Hz, 3H).
  • 9
  • [ 2016-42-4 ]
  • [ 1015423-45-6 ]
  • [ 1327275-53-5 ]
 

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