Ivacaftor
  • Ivacaftor

Ivacaftor | CAS 873054-44-5

  • cas：873054-44-5
  • Molecular Formula：C24H28N2O3
  • Purity：99%
  • Molecular Weight：392.498
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This product is for research and development use only.

Product Details;

CasNo： 873054-44-5

Molecular Formula： C24H28N2O3

Cost-effective and customizable Ivacaftor 873054-44-5 for sale

  • Molecular Formula:C24H28N2O3
  • Molecular Weight:392.498
  • Vapor Pressure:1E-12mmHg at 25°C 
  • Refractive Index:1.605 
  • Boiling Point:550.4 °C at 760 mmHg 
  • PKA:11.08±0.23(Predicted) 
  • Flash Point:286.7 °C 
  • PSA：85.68000 
  • Density:1.187 g/cm3 
  • LogP:5.46500 

VX-770(Cas 873054-44-5) Usage

Synthesis

Several patents describe a synthesis of ivacaftor, only one demonstrates the synthesis on scale and includes yields, which is depicted in the scheme. Beginning with treatment of commercial di-tert-butylphenol derivative 91 with ethyl chloroformate, the synthesis of carbonate 92 was achieved in quantitative yield. Nitration of 92 provided the desired nitroarene regioisomer 93 in 57% yield which was isolated by recrystallization. Reduction of the newlyinstalled nitro group and subsequent amide bond formation via reaction with commercially available acid chloride 94 produced amide 95 in 53% yield over the two step sequence. Finally, cleavage of the carbonate unmasked the phenol to furnish ivacaftor (XV) in 96% yield.

references

1. van goor f1, hadida s, grootenhuis pd, burton b, cao d, neuberger t, turnbull a, singh a, joubran j, hazlewood a, zhou j, mccartney j,arumugam v, decker c, yang j, young c, olson er, wine jj, frizzell ra, ashlock m, negulescu p. rescue of cf airway epithelial cell function in vitro by a cftr potentiator, vx-770. proc natl acad sci u s a. 2009 nov 3;106(44):18825-30. 2. vachel l1, norez c, becq f, vandebrouck c. effect of vx-770 (ivacaftor) and oag on ca2+ influx and cftr activity in g551d and f508del-cftr expressing cells. j cyst fibros. 2013 dec;12(6):584-91

Definition

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.

Brand name

Kalydeco

InChI:InChI=1/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)

873054-44-5Relevant academic research and scientific papers

Pharmaceutical compositions for the treatment of cystic fibrosis transmembrane conductance regulator mediated diseases

-

, (2021/04/21)

The present invention features compositions comprising a plurality of therapeutic agents wherein the presence of one therapeutic agent enhances the properties of at least one other therapeutic agent. In one embodiment, the therapeutic agents are cystic fibrosis transmembrane conductance regulators (CFTR) such as a CFTR corrector or CFTR potentiator for the treatment of CFTR mediated diseases such as cystic fibrosis. Methods and kits thereof are also disclosed.

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

-

Paragraph 00122, (2020/06/05)

This application describes methods of treating cystic fibrosis or a CFTR mediated disease comprising administering Compound I or a pharmaceutically acceptable salt thereof. (I) The application also describes pharmaceutical compositions comprising Compound I or a pharmaceutically acceptable salt thereof and optionally comprising one or more additional CFTR modulating agents.

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

-

Paragraph 00233, (2020/12/11)

This application describes methods of treating cystic fibrosis comprising administering Compound I:, a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising any of the foregoing.

Utilizing o-Quinone Methide Chemistry: Synthesis of d9-Ivacaftor

Lewandowski, Bérénice L.,Looker, Adam R.,Roeper, Stefanie,Ryan, Michael P.,Wilde, Nathan,Ye, Zhifeng

, (2020/01/22)

Lead time and cost are important factors for any pharmaceutical API. However, these issues become even more important when the drug substance contains an isotope such as deuterium, which has a natural abundance of only ～0.016% of all hydrogen. Fewer suppliers and logistical barriers both play a role in driving up the cost. These factors can challenge the supply route used to manufacture d9-ivacaftor (17), requiring investigation into alternative routes. By adapting the work from Pettus et al., a synthetic approach utilizing a transient o-quinone methide allowed access to the deuterium-labeled o-tert-butylphenol moiety. This was developed and proven on pilot scale to significantly reduce the number of deuterated reagents used, leading to an overall reduction in cost by a factor of 10, while also providing the substantial benefit of applying prior process knowledge from the parent, nonisotopically enriched API ivacaftor (7).

COMPOSITIONS AND METHODS FOR TREATMENT OF CYSTIC FIBROSIS

-

Paragraph 00324; 00325; 00333; 00342; 00343, (2019/01/22)

Compositions comprising Compound I of the formula (I) and methods of treating cystic fibrosis comprising administering Compound I. Compositions comprising a pharmaceutically acceptable salt of Compound I and methods of treating cystic fibrosis comprising administering a pharmaceutically acceptable salt of Compound I.

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

-

Paragraph 00152, (2019/02/06)

Methods of treating cystic fibrosis comprising administering at least Compound (I) of the formula. Pharmaceutical compositions containing a pharmaceutically acceptable salt of at least Compound I and methods of treating cystic fibrosis comprising administering a pharmaceutically acceptable salt of at least Compound (I).

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

-

Paragraph 00183, (2019/02/06)

Compound I of the formula (I) and/or pharmaceutically acceptable salt(s) of Compound I comprised in a pharmaceutical composition and methods of using the same to treat cystic fibrosis.

COMPOSITIONS FOR TREATING CYSTIC FIBROSIS

-

Paragraph 00250, (2019/06/23)

A single tablet comprising Compound I:. Methods of treating cystic fibrosis comprising administering one or more of such single tablets to a patient.

CRYSTALLINE FORMS AND COMPOSITIONS OF CFTR MODULATORS

-

Paragraph 0521; 0522, (2019/05/07)

Crystalline Forms of Compound I: and pharmaceutically acceptable salts thereofare disclosed. Pharmaceutical compositions comprising the same, methods of treating cystic fibrosis using the same, and methods for making the same are also disclosed.

CRYSTALLINE FORMS OF MODULATORS OF CFTR

-

Paragraph 00431, (2019/10/19)

Crystalline Forms of Compound (I); crystalline Forms of Compound (II) and crystalline forms of pharmaceutically acceptable salts of any of the foregoing are disclosed. Pharmaceutical compositions comprising the same, methods of treating cystic fibrosis using the same, and methods for making the same are also disclosed.

873054-44-5 Process route

C<sub>31</sub>H<sub>34</sub>N<sub>2</sub>O<sub>3</sub>

C31H34N2O3

ivacaftor
873054-44-5,1174930-71-2

ivacaftor

Conditions
Conditions Yield
With 5%-palladium/activated carbon; hydrogen; In methanol; at 35 ℃; for 5h; under 1520.1 Torr; Temperature; Pressure;
80%
5-amino-2-4-di-tert-butyl-phenol
873055-58-4

5-amino-2-4-di-tert-butyl-phenol

4-oxo-1,4-dihydroquinoline-3-carboxylic acid
13721-01-2

4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ivacaftor
873054-44-5,1174930-71-2

ivacaftor

Conditions
Conditions Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide;
71%
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 25 ℃; for 12h;
71%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;
71%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 15 - 30 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 15 - 30 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 20 ℃;
52%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 25 ℃; for 0.166667h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; at 25 ℃; for 12h;
46%
4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 0.5h;
5-amino-2-4-di-tert-butyl-phenol; In N,N-dimethyl-formamide; for 15h;
 

873054-44-5 Upstream products

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    5-amino-2-4-di-tert-butyl-phenol

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

  • 134271-94-6
    134271-94-6

    3-methyl-4-nitro-1H-indole

  • 1182822-31-6
    1182822-31-6

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

873054-44-5 Downstream products

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    [5-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-2,4-ditert-butyl-phenyl] 2-diethylaminoacetate

  • 1134821-98-9
    1134821-98-9

    ivacaftor 2-methylbutyric acid solvate

  • 1134821-99-0
    1134821-99-0

    N-(2,4-di-tert-butyl-5-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxamide propylene glycol solvate

  • 1134822-01-7
    1134822-01-7

    N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide.lactic acid

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