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Synthesis of coelenterazine

A technology for preparing cavities and benzyl groups, which is applied in the public domain and can solve problems such as reducing the practicality of the indication mechanism

Pending Publication Date: 2021-02-12
INT PAPER CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of visual indicators previously used to detect wetness in absorbent garments has a number of disadvantages in low light situations which greatly reduce the usefulness of their indicating mechanisms

Method used

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  • Synthesis of coelenterazine
  • Synthesis of coelenterazine
  • Synthesis of coelenterazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0174] Embodiment 1. the synthesis of coelenterazine (1 kilogram)

[0175] Synthesis of 3-Benzylpyrazin-2-amine (25)

[0176]

[0177] 10 L of toluene was added to a 100 L round bottom flask, followed by 10 L of tetramethylethylenedienylamine (TMEDA). The mixture was cooled to 0-5°C with ice water. Under nitrogen, at 1 to 1 1 / 2 To the stirred mixture was added dropwise 20 L of a solution of n-butyllithium (2.5M in n-hexane) at 0°C to 8°C over a period of hours. After the addition was complete, the reaction mixture was allowed to warm to room temperature (22°C). After standing at room temperature for 20 minutes, the mixture was slowly heated to 60° C. (butane gas was evolved during this time). The reaction mixture was maintained at 60°C ± 1°C for 30 minutes and then cooled to room temperature.

[0178] Simultaneously, tetrahydrofuran (THF) (15 L) and pyrazin-2-amine (24) (also known as 2-aminopyrazine (24)) (1 Kg) were added to another 30 L flask. The mixture wa...

Embodiment 2

[0204] Embodiment 2: the synthesis of coelenterazine (16)

[0205] 3-Benzyl-5-bromopyrazin-2-amine (2)

[0206]

[0207] Under an argon atmosphere, zinc powder and 30 mesh granular zinc (1:1, 16.05 / 16.05g, 491.2mmol, 3.5 equivalents) and I 2 (6.23 g, 5% of Zn) was added to a dry 1 L two necked round bottom flask. Add N,N'-dimethylacetamide (125mL, freshly treated with CaH 2 distillation). The mixture was stirred at room temperature until I 2 Brown color disappears. Benzyl bromide (61.04 g, 356.9 mmol, 2.5 equiv) was added dropwise, and the mixture was stirred at 80° C. for 4 hours. The mixture was cooled to room temperature, and 3,5-dibromo-2-aminopyrazine (1) (36.0 g, 140.3 mmol, 1 equiv) and PdCl were added 2 (PPh 3 ) 2 (5.04 g, 0.712 mmol, 5% of pyrazine) in N,N'-dimethylacetamide (150 mL). The mixture was continuously stirred under argon atmosphere for 1 day. Thin layer chromatography (TLC) (30% ethyl acetate / hexanes) showed the reaction was complete. The...

Embodiment 3

[0256] Example 3: Synthesis of coelenterazine hydrochloride, 100 gram scale

[0257] Starting material synthesis:

[0258] Starting materials 4-(5-amino-6-benzyl-pyrazin-2-yl)phenol (7) (53.0 g) and 1,1-diethoxy-3-(4-hydroxyphenyl)propane -2-Kone (14) (57.0 g) was synthesized by following the procedure previously described in Example 2.

[0259] 8-Benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-7H-imidazo[1,2-a]pyrazin-3-one (3)

[0260]

[0261] In a 1L round bottom flask equipped with a stir bar was added 4-(5-amino-6-benzyl-pyrazin-2-yl)phenol (7) (53.0 g, 191.25 mmol) followed by 1,4-di Oxane (275 mL). The resulting mixture was degassed and filled with argon. To the stirred mixture was added degassed 1:1 water / cone HCl (62.0 mL). The resulting mixture was again degassed and filled with argon and stirred at room temperature for 15 minutes. To this stirred suspension was added 1,1-diethoxy-3-(4-hydroxyphenyl)-2-propan-2-one (14) in degassed 1,4-dioxane (...

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Abstract

Disclosed herein are synthesis methods for coelenterazine. Also disclosed are articles including the coelenterazine and coelenterazine derivatives. Representative absorbent articles include disposablediapers and adult incontinence products.

Description

[0001] Cross References to Related Applications [0002] This application claims U.S. Provisional Application No. 62 / 845189, filed May 8, 2019, U.S. Provisional Application No. 62 / 692485, filed June 29, 2018, and U.S. Provisional Application No. 16, filed June 28, 2019 / 457788; each of these patent applications is expressly incorporated herein by reference in its entirety. Background technique [0003] Personal care absorbent products, such as baby diapers, adult incontinence pads and feminine care products, often contain a fluid-absorbent core. Many absorbent articles include a fluid-absorbent core disposed between a top sheet and a bottom sheet. The top sheet may be formed from a fluid permeable material adapted to facilitate fluid transfer into the absorbent core, for example when subjected to liquid insult, generally with minimal fluid retention on the top sheet. Southern American pine fluff pulp is commonly used in absorbent cores, generally in the form of a fibrous mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61F13/42
Inventor 拉贾戈帕拉·雷迪·杜武鲁拉马·巴特阿尼尔·库马尔
Owner INT PAPER CO
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