2-Amino-4-methoxybenzoic acid → 4-Fluoro-2-(4-((3S,5R)-5-(hydroxymethyl)pyrrolidin-3-ylamino)-7-methoxyquinazolin-2-yl)phenol

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Reaction Steps

The title compound was prepared using methods analogous to those described in Synthesis 80-A, 30-A, 76-B and 89-B, replacing 2-amino-5-methoxybenzoic acid with 2-amino-4-methoxybenzoic acid in Synthesis 80-A, replacing (S)-(−)-1-boc-3-aminopyrrolidine with (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester in Synthesis 30-A, replacing 2-hydroxyphenylboronic acid with 5-fluoro-2-hydroxyphenylboronic acid in Synthesis 76-B (using the crude Boc-protected amine in Synthesis 89-B), and replacing (2R,4S)-1-tert-butyl 2-methyl 4-(2-(5-fluoro-2-hydroxyphenyl)quinazolin-4-ylamino)pyrrolidine-1,2-dicarboxylate with (2R,4S)-1-tert-butyl 2-methyl 4-(2-(5-fluoro-2-hydroxyphenyl)-7-methoxyquinazolin-4-ylamino)pyrrolidine-1,2-dicarboxylate in Synthesis 89-B.

Provenance & Evidence