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A method of synthesizing c‑7280948

A technology of iridium complex and phenethylbenzenesulfonamide, which is applied in the field of synthesis of C-7280948, can solve the problems of low atom economy, impact on the environment, and poor stability, and achieve broad development prospects and high economic efficiency

Inactive Publication Date: 2018-04-03
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] These two methods all need multi-step reaction, and the reagent benzenesulfonyl chloride derivatives used are all highly toxic substances, have pungent odor, poor stability, and are easily converted into benzenesulfonic acid in air and water
A large number of by-products are generated during the reaction, which also seriously affects the environment
Atom economy of the reaction is low

Method used

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  • A method of synthesizing c‑7280948

Examples

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Embodiment 1

[0023]

[0024] Under nitrogen protection, 4-aminobenzenesulfonamide (172mg, 1mmol), [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), potassium hydroxide (56mg, 1mmol), and phenylethyl alcohol (610mg, 5equiv) were sequentially added to a 25mL Schlenk reaction flask. After the mixture was reacted at 120°C for 12 hours, it was cooled to room temperature, and the solvent was removed under reduced pressure in vacuo. Then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / n-hexane), yield: 80%.

[0025] mp 133-134°C; 1 H NMR (500MHz, DMSO-d 6 )δ7.40(d, J=8.3Hz, 2H, ArH), 7.26(t, J=7.2Hz, 2H, ArH), 7.21-7.10(m, 3H, ArH and 1H, NH), 6.60(d, J=8.3Hz,2H,ArH),5.90(s,2H,NH 2 ), 2.86 (quart, J=6.7Hz, 2H, NCH 2 ), 2.64(t, J=7.3Hz, 2H, CH 2 ); 13 C NMR (125MHz, DMSO-d 6 )δ152.4, 138.9, 128.6, 128.4, 128.3, 126.1, 125.3, 112.6, 44.1, 35.2.

Embodiment 2

[0027] Except replacing potassium hydroxide with sodium hydroxide (40mg, 1mmol, 1equiv.), other reaction raw materials, conditions and products are the same as Example 1, and the productive rate: 75%

Embodiment 3

[0029] Except replacing potassium hydroxide with potassium tert-butoxide (42.4mg, 0.2mmol, 0.2equiv.), other reaction raw materials, conditions and products are the same as in Example 1, and the yield: 79%

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Abstract

The invention discloses a method for synthesizing C-7280948. Comprise the following steps: in reaction vessel, add 4-aminobenzenesulfonamide, phenethyl alcohol, iridium complex catalyst and alkali, after reaction mixture reacts several hours at 100-120 o C, be cooled to room temperature, rotary evaporation removes solvent, Then separated by column to obtain the target compound. The invention uses commercialized 4-aminobenzenesulfonamide and almost non-toxic alcohol as starting materials; the reaction only generates water as a by-product, without environmental hazard; and the reaction atom is economical.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a method for synthesizing C-7280948. Background technique [0002] PRMT1 belongs to type I PRMT enzymes, the molecular size is about 40kDa, and it often functions in the form of macromolecular complexes. There are many substrate molecules, and the enzyme activity is regulated by many factors. PRMT1 is involved in various cellular processes such as cell signal transduction, DNA damage repair, transcription regulation, RNA metabolism, and protein interaction. PRMT1 is associated with a variety of cancerous and non-cancerous diseases. C-7280948 (4-amino-N-phenethylbenzenesulfonamide) is a very promising class of PRMT1 inhibitors, which has made important progress in the treatment of diseases. ((a) Itoh Y et al. Small-molecular modulators of cancer-associated epigenetic mechanisms. Mol Biosyst 9:873-96 (2013). (b) Bissinger EM et al. Acyl derivatives...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/44C07C303/40
Inventor 李峰
Owner NANJING UNIV OF SCI & TECH
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