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Product Details of [ 76074-88-9 ]

CAS No. :	76074-88-9	MDL No. :	MFCD06203948
Formula :	C₂₄H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	368.43	Pubchem ID :	-
Synonyms :

Safety of [ 76074-88-9 ]

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Application In Synthesis of [ 76074-88-9 ]

* 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 [ 76074-88-9 ]

[ 76074-88-9 ] Synthesis Path-Downstream 1~5

1
[ 596-43-0 ]
[ 17325-26-7 ]
[ 76074-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 5h;	Methyl (1-N-triphenylmethyl)imidazole-4-carboxylate (5B). To a suspension of methyl 4-imidazole carboxylate (0.5 g, 3.96 mmol) in DMF (4 mL) was added triethylamine (0.828 mL, 5.94 mmol) and triphenylmethyl bromide (1.54 g, 4.76 mmol) at 0 C. under argon. The reaction mixture was allowed to warm to ambient temperature and stirred for 5 h. The reaction was then quenched with water and the mixture was extracted with ethyl acetate. The organic extraxt was washed with brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The resultant residue was purified by flash chromatograph on silica gel (hexane/ethyl acetate) to give 5B. 1H NMR (400 MHz, CDCl3) delta 7.58 (d, 1H), 7.46 (d, 1 H), 7.33-7.38 (m, 9 H), 7.10-7.14(m, 6 H), 3.87 (s, 3 H).

Reference： [1]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 1051 - 1056
[2]Patent: US2003/229079,2003,A1 .Location in patent: Page 36-37

2
[ 17325-26-7 ]
[ 76-83-5 ]
[ 76074-88-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	Methyl 1H-imidazole-4-carboxylate (96.5 g, 765.1 mmol) was dissolved in 1.8 LIn N,N-dimethylformamide (DMF), then triphenylchloromethane (213.3 g, 765.1 mmol) was added.Finally, triethylamine (85.2 g, 841.6 mmol) was added.After the addition, the nitrogen was replaced three times, and the reaction was carried out at room temperature for about 2 hours.The TLC detects the completion of the reaction and terminates the reaction. Post processing:The reaction system was slowly poured into 6 L of water, stirred and lysed for 1.0 h, filtered, and the filter cake was washed with 500 ml of water.Drying at 50 C for 4 h gave 282.0 g of an off-white solid in a yield of 100.0%.
100%	With triethylamine; In dichloromethane; at 25℃; for 1h;Inert atmosphere;	Methyl 4-1H-imidazolecarboxylate (Compound 14, manufactured by Wako Pure Chemical Industries, Ltd.) (2.0 g, 15.9 mmol) was dissolved in dichloromethane (70 mL), triethylamine (2.66 mL, 17.5 mmol) Trityl chloride (4.88 g, 19.1 mmol) was added, and the mixture was stirred at room temperature (25 C.) for 1 hour under an argon gas atmosphere. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1 ? 1/1) to obtain Compound 15 5.86 g, 15.9 mmol, determined quantitatively)
98.6%	With triethylamine; In ethyl acetate; N,N-dimethyl-formamide;	Step 1 Preparation of 1-trityl-1H-imidazole-4-carboxylic acid methyl ester A solution of 1H-Imidazole-4-carboxylic acid methyl ester (1.0 g, 7.93 mmol) in N,N-dimethylformamide at 25 C. was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 mmol). The reaction was stirred at 25 C. for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50:50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.88 g, 98.6%) as a white foam: 1H NMR (DMSO-d6, 300 MHz) delta7.56 (s, 1H), 7.47 (m, 10H), 7.09 (m, 6H), 3.69 (s, 3H).

98.6%	With triethylamine; In DMF (N,N-dimethyl-formamide); at 25℃; for 8h;	A solution of [1H-IMIDAZOLE-4-CARBOXYLIC] acid methyl ester (1.0 g, 7.93 mmol) in [N, N] dimethylformamide at [25 oC] was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 [MMOL).] The reaction was stirred at [25 oC] for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a IN aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230- 400 mesh, 50: 50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4- carboxylic acid methyl ester (2. [88] g, 98.6%) as a white foam
86%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	For methyl 1-tritylimidazole-4-carboxylate (6), trityl chloride(1.77 g, 6.35 mmol) was first stirred into a solution of 5 (0.80 g,6.3 mmol) in DMF (20 mL) under N2. NEt3 (0.98 mL, 7.0 mmol) wasthen added, and the mixture stirred for 16 h at r.t. before being pouredover ice; the cold mixture was then filtered and the isolated solid waswashed with H2O (2 × 5 mL), and then dried in vacuo at r.t. for 24 h.Yield: 2.01 g (86%). 1H NMR (CDCl3): delta 7.65 (s, 1H, H5-Im), 7.52 (s, 1H,H2-Im), 7.03-7.36 (m, 15H, Ph3C), 2.42 (s, 3H, CH3-Im). ESI-MS: 369(M+), 243 (CPh3). Anal. Calcd. for C24H20N2O2: C, 78.24; H, 5.47; N,7.60. Found: C, 78.35; H, 5.6; N, 7.4.
	With triethylamine; In acetonitrile; at 20℃;	Preparation 121 1-Trityl- 1H-imidazole-4-carboxylic acid methyl ester Add triethylamine (1.88 mL, 13.48 mmol) to a mixture of methyl-4-imidazolecarboxylate (1.0 g, 7.93 mmol) and triphenylmethyl chloride (2.43 g, 8.72 mmol) in anhydrous acetonitrile (25 mL) over 10 min at room temperature and stir overnight. Quench with water and extract with ethyl acetate (3*). Combine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially, dry over sodium sulfate, and concentrate to provide the title compound 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol).

Reference： [1]Patent: CN108314654,2018,A .Location in patent: Paragraph 0090-0092
[2]Patent: JP2015/93831,2015,A .Location in patent: Paragraph 0016; 0088; 0090
[3]Patent: US2004/14766,2004,A1
[4]Patent: WO2003/106459,2003,A1 .Location in patent: Page 111
[5]Inorganic Chemistry Communications,2017,vol. 78,p. 32 - 36
[6]Journal of Medicinal Chemistry,2010,vol. 53,p. 1712 - 1725
[7]Patent: US2010/16373,2010,A1 .Location in patent: Page/Page column 17

3
[ 76074-88-9 ]
[ 191103-80-7 ]

Yield	Reaction Conditions	Operation in experiment
95.1%	With aqueous hydrochloric acid; aqueous sodium hydroxide In methanol	67.2 Step 2 Step 2 Preparation of 1-trityl-1H-imidazole-4-carboxylic acid A solution of 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (1.75 g, 4.60 mmol) in methanol (50 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (13.8 mL, 13.8 mmol). The reaction was stirred at 25° C. for 18 h and then heated to 50° C. for 1.5 h. At this time, the reaction was cooled to 25° C. and diluted with water (150 mL). The aqueous layer was brought to pH=1 by treatment with a 1N aqueous hydrochloric acid solution and then diluted with ethyl acetate (250 mL). The resulting precipitated product was collected by filtration. The filtrate was extracted with ethyl acetate (1150 mL). The combined organics were then washed with a saturated aqueous sodium chloride solution (1100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The two batches of product were combined to afford 1-trityl-1H-imidazole-4-carboxylic acid (1.55 g, 95.1%.) as a white solid: LR-MS for C23H18N2O2 (M+H)+ at m/z=355.
95.1%	Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With sodium hydroxide; water In methanol at 25 - 50℃; for 19.5h; Stage #2: With hydrogenchloride In methanol; water at 25℃;	67.2 Step 2: Preparation of 1-trityl-1H-imidazole-4-carboxylic acid A solution of [L-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid methyl ester (1.75 g, 4.60 mmol) in methanol (50 mL) at [25 oC] was treated with a IN aqueous sodium hydroxide solution (13.8 mL, 13.8 [MMOL).] The reaction was stirred at [25 oC] for 18 h and then heated to [50 oC] for 1.5 h. At this time, the reaction was cooled to [25 oC] and diluted with water (150 mL). The aqueous layer was brought to pH=l by treatment with a IN aqueous hydrochloric acid solution and then diluted with ethyl acetate (250 mL). The resulting precipitated product was collected by filtration. The filtrate was extracted with ethyl acetate [(1] x 150 mL). The combined organics were then washed with a saturated aqueous sodium chloride solution [(1] x 100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The two batches of product were combined to afford [L-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid (1.55 g, 95.1%.) as a white solid:
	Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 5h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water	122 1-Trityl-1 H-imidazole-4-carboxylic acid Preparation 122 1-Trityl-1 H-imidazole-4-carboxylic acid Add 1N sodium hydroxide (22.8 mL, 22.8 mmol) to 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) at room temperature. Stir the reaction mixture at room temperature for 5 hrs. Acidify the reaction mixture with 5N aqueous hydrochloride to pH about 6. Filter and dry the solid to give the title compound as a white solid (2 g, 5.64 mmol).

Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With water; lithium hydroxide In methanol at 20℃; Stage #2: With hydrogenchloride In methanol; water

A.41 3H-Imidazole-4-carboxylic acid methyl ester (9.86 g, 78.2 mmol) is taken up in 150 mL DCM, triethylamine (11.9 mL, 86.0 mmol) is added and the reaction mixture is stirred for 5 min. at RT. Chlorotriphenylmethane (24.0 g, 86.0 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is extracted with an aqueous 5% NaHCOs solution, the organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue (20.7 g) is taken up in 100 rnL MeOH, a solution of lithium hydroxide (4.80 g, 24.0 mmol) in 20 rnL water is added drop wise and the reaction mixture is stirred over weekend at RT. The reaction mixture is acidified to pH 4 with 6N hydrochloric acid, 200 mL DCM is added and the two phase mixture is stirred vigorously. The phases are separated and the organic phase is dried over MgSO4 and concentrated under reduced pressure. Yield: 19.2 g. HPLC-MS: double peak tR = 2.55/2.67 min, (M-H)" = 353.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2004/14766, 2004, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2003/106459, 2003, A1 Location in patent: Page 111
[3]Current Patent Assignee: ELI LILLY & CO - US2010/16373, 2010, A1 Location in patent: Page/Page column 17
[4]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2010/122071, 2010, A1 Location in patent: Page/Page column 29-30

4
[ 76074-88-9 ]
[ 89892-38-6 ]
methyl 1-(3-bromo-4-cyanobenzyl)-1H-imidazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		Compound 15 (200 mg, 0.543 mmol) obtained in Step 3 - 2 was dissolved in acetonitrile (5.0 mL), and the compound 13 (149 mg, 0.543 mmol) obtained in Step 3 - 1 was added thereto, and an argon gas atmosphere And heated under reflux for 18 hours. The reaction solution was concentrated under reduced pressure, methanol (5 mL) and diethylamine (200 μL) were added and the mixture was further heated under reflux for 2 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain CDP 1350 (68.0 mg, 0.212 mmol, yield 39% ) Was obtained.

Reference： [1]Patent: JP2015/93831,2015,A .Location in patent: Paragraph 0016; 0088; 0091

5
[ 62938-08-3 ]
[ 76074-88-9 ]
methyl 1-(3,5-di-tert-butylphenyl)-1 H-imidazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 3,5-di-tert-butylbenzyl bromide; methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate In acetonitrile Reflux; Inert atmosphere; Stage #2: With diethylamine In methanol; acetonitrile for 1h; Reflux; Inert atmosphere;	5 Example 5: Synthesis of CDP 1500 CDP 1500 (compound 20) was synthesized according to the scheme shown in FIG.Compound 15 (100 mg, 0.271 mmol) obtained in step 3 - 2 of Example 3 was dissolved in acetonitrile (3.0 mL) and 3,5-di-tert-butylbenzyl bromide (92.1 mg, 0 .325 mmol) was added. And heated under reflux overnight in an argon gas atmosphere. After completion of the reaction, the mixture was concentrated under reduced pressure, methanol (3.0 mL) and diethylamine (0.15 mL) were added to the resulting crude product, and the mixture was heated under reflux for 1 hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 2/1) to give CDP 1200 (57.3 mg, 0.174 mmol, yield 64%).

Reference： [1]Current Patent Assignee: KYOTO UNIVERSITY; GENERAL ELECTRIC CO; SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - JP2015/93831, 2015, A Location in patent: Paragraph 0016; 0095

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[ CAS No. 76074-88-9 ] {[proInfo.proName]}

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[ 76074-88-9 ] Synthesis Path-Downstream 1~5

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

Inquiry