ChemicalBook CAS DataBase List Carbonic acid 5-[[(1,4-dihydro-4-oxo-3-quinolinyl)carbonyl]amino]-2,4-bis(1,1-dimethylethyl)phenyl methyl ester

Carbonic acid 5-[[(1,4-dihydro-4-oxo-3-quinolinyl)carbonyl]amino]-2,4-bis(1,1-dimethylethyl)phenyl methyl ester synthesis

12synthesis methods

Product Name:Carbonic acid 5-[[(1,4-dihydro-4-oxo-3-quinolinyl)carbonyl]amino]-2,4-bis(1,1-dimethylethyl)phenyl methyl ester
CAS Number:1246213-45-5
Molecular formula:C26H30N2O5
Molecular Weight:450.53

5-amino-2,4-di-tert-butylphenyl methyl carbonate

1182822-31-6
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13721-01-2 Synthesis

4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

13721-01-2
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Carbonic acid 5-[[(1,4-dihydro-4-oxo-3-quinolinyl)carbonyl]amino]-2,4-bis(1,1-dimethylethyl)phenyl methyl ester

1246213-45-5
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Yield:1246213-45-5 67%

Reaction Conditions:

Stage #1: 1,4-dihydro-4-oxo-quinoline-3-carboxylic acid esterwith N-ethyl-N,N-diisopropylamine;O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate in N,N-dimethyl-formamide at 25; for 0.333333 h;
Stage #2: 5-amino-2,4-di-tert-butylphenyl methyl carbonate in N,N-dimethyl-formamide at 70; for 2 h;

Steps:

7 Synthesis of 2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate

To a solution of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (23.5 g, 121mmol) in DMF (400 mL) at 25°C were added HATU (57.2 g, 150 mmol) and DIEA (23.91 g, 185 mmol). The reaction was stirred for 20 min and 5 -amino-2, 4-di-tert-butylphenyl methyl carbonate (38 g, 116 mmol) was added. The reaction was stirred at 70 °C for 2 h, allowed to cool to 25 °C and poured into water (100 mL). The mixture was filtered, and the filtrate concentrated in vacuo. The residue was triturated with petroleum ether/ethyl acetate 3:1 (80 mL) to give the title compound as an off-white solid. Yield 40 g (67%).¹H NMR (400 MHz, DMSO-d₆): δ 12.00 (s, 1H), 8.88-8.85 (m, 1H), 8.35-8.33 (m, 1H), 7.82-7.79 (m, 1H), 7.76-7.74 (m, 1H), 7.59 (s, 1H), 7.54-7.52 (m, 1H), 7.39 (s, 1H), 4.80 (s, 1H), 3.85-3.79 (m, 3H), 1.46 (s, 9H), 1.32 (s, 9H). m/z: [ESI+]785.2 (M+H)⁺, (C₂₀H₃₀N₂O₅).

References:

WO2022/148822,2022,A1 Location in patent:Paragraph 00572-00574

96-76-4 Synthesis