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Process for preparing resorcinol derivatives

  • US 6,504,037 B2
  • Filed: 03/08/2001
  • Issued: 01/07/2003
  • Est. Priority Date: 03/15/2000
  • Status: Expired due to Fees
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Assignment
First Claim
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1. A compound having the structure of formula (5), embedded imagewherein Q is halo;

  • wherein W is hydrogen or a protecting group; and

    wherein X and Y are each independently selected from hydrogen, (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, or X and Y are taken together with the carbon to which they are attached to form a (C4-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, provided that the (C4-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring is not aromatic;

    and wherein the (C1-C12)alkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C4-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring is optionally substituted by one to three independently selected groups Z, where Z is selected from the group consisting of cyano;

    halo;

    (C1-C6)alkyl;

    aryl;

    (C2-C9)heterocycloalkyl;

    (C2-C9)heteroaryl;

    aryl(C1-C6)alkyl-;

    ═

    O;

    ═

    CHO(C1-C6)alkyl;

    amino;

    hydroxy;

    (C1-C6)alkoxy;

    aryl(C1-C6)alkoxy-;

    (C1-C6)acyl;

    (C1-C6)alkylamino-;

    aryl(C1-C6)alkylamino-;

    amino(C1-C6)alkyl-;

    (C1-C6)alkoxy-CO—

    NH—

    ;

    (C1-C6)alkylamino-CO—

    ;

    (C2-C6)alkenyl;

    (C2-C6)alkynyl;

    hydroxy(C1-C6)alkyl-;

    (C1-C6)alkoxy(C1-C6)alkyl-;

    (C1-C6)acyloxy(C1-C6)alkyl-;

    nitro;

    cyano(C1-C6)alkyl-;

    halo(C1-C6)alkyl-;

    nitro(C1-C6)alkyl-;

    trifluoromethyl;

    trifluoromethyl(C1-C6)alkyl-;

    (C1-C6)acylamino-;

    (C1-C6)acylamino(C1-C6)alkyl-;

    (C1-C6)alkoxy(C1-C6)acylamino-;

    amino(C1-C6)acyl-;

    amino(C1-C6)acyl(C1-C6)alkyl-;

    (C1-C6)alkylamino(C1-C6)acyl-;

    ((C1-C6) alkyl)2amino(C1-C6)acyl-;

    —

    CO2R2;

    —

    (C1-C6)alkyl-CO2R2, —

    C(O)N(R2)2;

    —

    (C1-C6)alkyl-C(O)N(R2)2;

    R2ON═

    ;

    R2ON═

    (C1-C6)alkyl-;

    R2ON═

    CR2(C1-C6)alkyl-;

    —

    NR2(OR2);

    —

    (C1-C6)alkyl-NR2(OR2);

    —

    C(O)(NR2OR2);

    —

    (C1-C6)alkyl-C(O)(NR2OR2);

    —

    S(O)mR2;

    wherein each R2 is independently selected from hydrogen, (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;

    R3C(O)O—

    , wherein R3 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;

    R3C(O)O—

    (C1-C6)alkyl-;

    R4R5N—

    C(O)—

    O—

    ;

    R4R5NS(O)2—

    ;

    R4R5NS(O)2(C1-C6)alkyl-;

    R4S(O)2R5N-;

    R4S(O)2R5N(C1-C6)alkyl-;

    wherein m is 0, 1 or 2, and R4 and R5 are each independently selected from hydrogen or (C1-C6)alkyl;

    —

    C(═

    NR6)(N(R4)2);

    —

    (C1-C6)alkyl-C(═

    NR6)(N(R4)2) wherein R6 represents OR2 or R2 wherein R2 is defined as above;

    —

    OC(O)aryl(C1-C6)alkyl;

    —

    NH(C1-C6)alkyl;

    aryl(C1-C6)alkyl-HN—

    ; and

    a ketal.

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