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ChemicalBook CAS DataBase List Ivacaftor
873054-44-5

Ivacaftor synthesis

7synthesis methods
Ivacaftor, also known as VX-770, is a drug used to treat cystic fibrosis in people with certain mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) gene, who account for 4–5% cases of cystic fibrosis, and is included in a combination drug, lumacaftor/ivacaftor, which is used to treat people with cystic fibrosis who have the F508del mutation in CFTR. Ivacaftor is a "potentiator" of CFTR, meaning it increases the probability that the defective channel will be open and allow chloride ions pass through the channel pore. Synthetic Description Reference: Zhang, Rui; Han, Guanyu; Jiang, Luobin; Shen, Yao; Yang, Rui; Mao, Yongjun; Wang, Hang. An Efficient Synthesis of Ivacaftor. Journal of Heterocyclic Chemistry. Volume 54. Issue 6. Pages 3169-3173. Journal; Online Computer File. (2017). Synthetic Description Reference: Hadida, Sabine; Van Goor, Fredrick; Zhou, Jinglan; Arumugam, Vijayalaksmi; McCartney, Jason; Hazlewood, Anna; Decker, Caroline; Negulescu, Paul; Grootenhuis, Peter D. J. Discovery of N-(2,4-Di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, Ivacaftor), a Potent and Orally Bioavailable CFTR Potentiator. Journal of Medicinal Chemistry. Volume 57. Issue 23. Pages 9776-9795. Journal; Online Computer File. (2014). Synthetic Description Reference: He, Yang; Xu, Qien; Ma, Wenpeng; Zhang, Jian; Sun, Hongbing; Shen, Jingshan. Expeditious synthesis of ivacaftor. Heterocycles. Volume 89. Issue 4. Pages 1035-1040. Journal. (2014). Synthetic Description Reference: Vasudevan, N.; Jachak, Gorakhnath R.; Reddy, D. Srinivasa. Breaking and Making of Rings: A Method for the Preparation of 4-Quinolone-3-carb-oxylic Acid Amides and the Expensive Drug Ivacaftor. European Journal of Organic Chemistry. Volume 2015. Issue 34. Pages 7433-7437. Journal; Online Computer File. (2015).
Synthetic Routes
  • ROUTE 1

    • 202112070672277416.jpg

    Reference: Zhang, Rui; Han, Guanyu; Jiang, Luobin; Shen, Yao; Yang, Rui; Mao, Yongjun; Wang, Hang. An Efficient Synthesis of Ivacaftor. Journal of Heterocyclic Chemistry. Volume 54. Issue 6. Pages 3169-3173. Journal; Online Computer File. (2017).

  • ROUTE 2

    • 202112070244625139.jpg

    Reference: Hadida, Sabine; Van Goor, Fredrick; Zhou, Jinglan; Arumugam, Vijayalaksmi; McCartney, Jason; Hazlewood, Anna; Decker, Caroline; Negulescu, Paul; Grootenhuis, Peter D. J. Discovery of N-(2,4-Di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, Ivacaftor), a Potent and Orally Bioavailable CFTR Potentiator. Journal of Medicinal Chemistry. Volume 57. Issue 23. Pages 9776-9795. Journal; Online Computer File. (2014).

  • ROUTE 3

    • 202112076652538587.jpg

    Reference: He, Yang; Xu, Qien; Ma, Wenpeng; Zhang, Jian; Sun, Hongbing; Shen, Jingshan. Expeditious synthesis of ivacaftor. Heterocycles. Volume 89. Issue 4. Pages 1035-1040. Journal. (2014).

  • ROUTE 4

    • 202112073594946558.jpg

    Reference: Vasudevan, N.; Jachak, Gorakhnath R.; Reddy, D. Srinivasa. Breaking and Making of Rings: A Method for the Preparation of 4-Quinolone-3-carb-oxylic Acid Amides and the Expensive Drug Ivacaftor. European Journal of Organic Chemistry. Volume 2015. Issue 34. Pages 7433-7437. Journal; Online Computer File. (2015).

202112070672277416.jpg

Reference: Zhang, Rui; Han, Guanyu; Jiang, Luobin; Shen, Yao; Yang, Rui; Mao, Yongjun; Wang, Hang. An Efficient Synthesis of Ivacaftor. Journal of Heterocyclic Chemistry. Volume 54. Issue 6. Pages 3169-3173. Journal; Online Computer File. (2017).

1246213-45-5 Synthesis
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:873054-44-5 76%

Reaction Conditions:

with water;sodium hydroxide in methanol at 20; for 5 h;

Steps:

28 Example 28: Synthesis of ivacaftor (26):
To a solution of 2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate 5 (30 mg, 0.06mmol) in MeOH (2 mL) was added NaOH (5.3 mg, 0.13mmol) dissolved in H2O (2 mL), and the reaction mixture was stirred at room temperature for 5h. Reaction mass was evaporated to one third of its volume (temperature not exceeding 40°C) and acidified with aq.2N HC1 to pH 2-3. The resulting precipitate was collected by suction filtration give desired compound 7 (19 mg, 76%) as off white solid. 1H NMR (400MHz, DMSO-d6) δ = 12.88 (d, J = 6.6 Hz, 1 H), 11.81 (s, 1 H), 9.20 (s, 1 H), 8.86 (d, J = 6.6 Hz, 1 H), 8.32 (d, J = 7.8 Hz, 1 H), 7.88 - 7.65 (m, 2 H), 7.51 (t, J = 7.5 Hz, 1 H), 7.16 (s, 1 H), 7.10 (s, 1 H), 1.38 (s,9H), 1.36 (s, 9H).

References:

COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH;REDDY, Dumbala Srinivasa;NATARAJAN, Vasudevan;JACHAK, Gorakhnath Rajaram WO2016/181414, 2016, A1 Location in patent:Paragraph 066

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