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N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6- [5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Ditosylate

IP.com Disclosure Number: IPCOM000201703D
Publication Date: 2010-Nov-18
Document File: 3 page(s) / 21K

Publishing Venue

The IP.com Prior Art Database

Abstract

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This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 52% of the total text.

Page 01 of 3

      N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6- [5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Ditosylate

N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino) methyl]-2-furyl]quinazolin-4-amine Ditosylate has the following chemical structure:

O

x 2 HO3S CH3

Example 1 - Preparation of N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5- [(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Ditosylate N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino) methyl]-2-furyl]quinazolin-4-amine Ditosylate, previously isolated as known from the literature solid (wet or dry) Anhydrate (Form A) or any other solid form, can be re- crystallized from 40-100 volumes of aqueous solution of polar organic solvents such as C1-C4 alcohols, acetone, methyl ethyl ketone, DMF, DMA, acetonitrile, THF, Methyl- THF, 1,4-dioxane or mixture thereof and converted into N-[3-Chloro-4-[(3- fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl] quinazolin-4-amine Ditosylate Monohydrate (Form M) in high yield and good chemical quality. The procedure contains full or almost full dissolving of the starting material in the organic solvent mixture with water under heating, cooling for precipitation and N-[3- Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2- furyl]quinazolin-4-amine Ditosylate Monohydrate (Form M) filtration.

S

O

O

Cl

F

HN

HN

N

O

N



Page 02 of 3

Example 2 - Preparation of N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5- [(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Ditosylate N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino) methyl]-2-furyl]quinazolin-4-amine Ditosylate, previously isolated as known from the literature solid (wet or dry) Anhydrate (Form A) or any other solid form, can be triturated in 10-40 volumes of aqueous solution of polar organic solvents such as C1-C4 alcohols, acetone, methyl ethyl ketone, DMF, DMA, acetonitrile, THF, Methyl-THF, 1,4-dioxane or mixture thereof and converted into N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5- [(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Ditosylate Monohydrate (Form M) in high yield and good c...