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[ CAS No. 299912-59-7 ] {[proInfo.proName]}

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Chemical Structure| 299912-59-7
Chemical Structure| 299912-59-7
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Product Details of [ 299912-59-7 ]

CAS No. :299912-59-7 MDL No. :
Formula : C25H30ClN3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 487.98 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 299912-59-7 ]

* 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 [ 299912-59-7 ]

[ 299912-59-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 69088-96-6 ]
  • [ 183322-18-1 ]
  • [ 299912-59-7 ]
YieldReaction ConditionsOperation in experiment
100% In acetonitrile at 25℃; for 5h; Inert atmosphere; Reflux; 9 Example 9 - Synthesis of 3-Butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine] phenyl]-2-methyl-, hydrochloride (1:1) of formula (II) - exemplifying the invention.; Synthesis scheme [Show Image] In a 500 ml flask provided with a thermometer there are introduced - in succession at 25°C and under nitrogen atmosphere - 1 5 g of 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline of formula (III), 9.2 g of 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol of formula (IV) and 225 mL of Acetonitrile. The mixture is heated at reflux for 5 hours. Upon completing the reaction the mixture is cooled to 0-5°C and maintained at that temperature under stirring for at least 1 hour. The suspension is filtered and the solid is washed using 15 mL of cold Acetonitrile. The product is dried under vacuum for at least 8 hours obtaining 23.4 g of product as a white solid for a molar yield equivalent to 100%.
100% In acetonitrile for 5h; Inert atmosphere; Reflux; 9 Synthesis of 3-Butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl-, hydrochloride (1:1) of formula (II)-exemplifying the invention Example 9 Synthesis of 3-Butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl-, hydrochloride (1:1) of formula (II)-exemplifying the invention In a 500 ml flask provided with a thermometer there are introduced-in succession at 25° C. and under nitrogen atmosphere-15 g of 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline of formula (III), 9.2 g of 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol of formula (IV) and 225 mL of Acetonitrile. The mixture is heated at reflux for 5 hours. Upon completing the reaction the mixture is cooled to 0-5° C. and maintained at that temperature under stirring for at least 1 hour. The suspension is filtered and the solid is washed using 15 mL of cold Acetonitrile. The product is dried under vacuum for at least 8 hours obtaining 23.4 g of product as a white solid for a molar yield equivalent to 100%.
  • 2
  • [ 299912-59-7 ]
  • [ 183319-69-9 ]
YieldReaction ConditionsOperation in experiment
74% Example 10 - Synthesis of Erlotinib hydrochloride of formula (I) - exemplifying the invention.; Synthesis scheme [Show Image] In a 500 ml flask provided with a thermometer there are introduced - in succession at 25C and under nitrogen atmosphere - 32.3 g of 3-Butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine] phenyl]-2-methyl-, hydrochloride (1:1) of formula (II), 300 mL of purified water and 600 mL of n-butanol. It is stirred at ambient temperature for 30 minutes. 50% aqueous NaOH is added up to a 10-12 pH. A limpid two-phase system is obtained. The phases are separated and the organic phase is concentrated at atmospheric pressure (thus azeotropically removing water) up to a residual volume of 300 mL. Thus 0.13 g of anhydrous solid NaOH are added and the resulting mixture is heated at reflux to 115-120C for 24 hours. Thus 150 mL of n-butanol are removed and the concentrated mixture is cooled to 15-25C. A solution of 6.1 mL of concentrated HCl and 60 mL of n-butanol are thus dripped maintaining the temperature below 25C. The obtained suspension is left under stirring over the whole night at 20-25C. The suspension is filtered and the solid is washed using 25 mL of n-butanol. The solid is dried under vacuum at 45-50C. 21 g of Erlotinib hydrochloride are obtained for a molar yield equivalent to 74%.
  • 3
  • [ 299912-59-7 ]
  • [ 67-64-1 ]
  • [ 183319-69-9 ]
YieldReaction ConditionsOperation in experiment
Example 10 Synthesis of Erlotinib Hydrochloride of Formula (I)-Exemplifying the Invention In a 500 ml flask provided with a thermometer there are introduced-in succession at 25 C. and under nitrogen atmosphere-32.3 g of 3-Butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl-, hydrochloride (1:1) of formula (II), 300 mL of purified water and 600 mL of n-butanol. It is stirred at ambient temperature for 30 minutes. 50% aqueous NaOH is added up to a 10-12 pH. A limpid two-phase system is obtained. The phases are separated and the organic phase is concentrated at atmospheric pressure (thus azeotropically removing water) up to a residual volume of 300 mL. Thus 0.13 g of anhydrous solid NaOH are added and the resulting mixture is heated at reflux to 115-120 C. for 24 hours. Thus 150 mL of n-butanol are removed and the concentrated mixture is cooled to 15-25 C. A solution of 6.1 mL of concentrated HCl and 60 mL of n-butanol are thus dripped maintaining the temperature below 25 C. The obtained suspension is left under stirring over the whole night at 20-25 C. The suspension is filtered and the solid is washed using 25 mL of n-butanol. The solid is dried under vacuum at 45-50 C. 21 g of Erlotinib hydrochloride are obtained for a molar yield equivalent to 740.
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