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ChemicalBook CAS DataBase List Erlotinib hydrochloride
183319-69-9

Erlotinib hydrochloride synthesis

11synthesis methods
The synthesis of this agent is based on the original patent and is shown in the Scheme. The 3,4-dihydroxy benzoate 31 was reacted with bromoethyl methyl ether in the presence of potassium carbonate and tetrabutyl ammonium iodide to give 32 in 93% yield. Nitration followed by hydrogenation provided 34 in 88% yield, which was then cyclized in formamide with ammonium formate to provide quinazolone 35. Subsequent reaction with oxalyl chloride gave quinazoline chloride 36, which was then reacted with 3-ethynyl aniline (37) in isopropanol in the presence of pyridine to give the desired product erlotinib, which was isolated as the HCl salt (V). An alternate synthesis, that used protected 3-trimethylsilyl ethynyl aniline to couple to the quinazoline chloride 36, has also been published.

183321-74-6 Synthesis
Erlotinib

183321-74-6
398 suppliers
$5.00/25mg

-

Yield:183319-69-9 100%

Reaction Conditions:

with hydrogenchloride in isopropyl alcohol at 0; for 1 h;Product distribution / selectivity;Inert atmosphere;

Steps:

1

Example 1 : Erlotinib free base (180 g) containing 15% w/w isopropyl alcohol (IPA) was charged into a three necked flask under nitrogen and cooled to O0C. The solid was exposed to hydrogen chloride gas for about 1 hour to form the hydrochloride salt with stirring. The erlotinib hydrochloride was then dried at 2O0C to 250C in a vacuum oven. The yield was quantitative. 1H NMR (DMSO-d6): ￡3.36 (s, 6H), 3.79 (m, 4H), 4.28 (s, 1 H), 4.31 (t, J = 4.6 Hz, 2H),4.41 (t, J = 4.8 Hz, 2H), 7.39-7.43 (m, 2H), 7.48 (t, J = 7.9 Hz, IH), 7.82 (d, J = 8.4 Hz, 1 H), 7.90 (s, 1 H), 8.51 (s, 1 H), 8.83 (s, 1 H), 1 1.68 (s, 1 H).

References:

WO2010/40212,2010,A1 Location in patent:Page/Page column 8

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