Synthesis of mavorixafor and intermediates thereof

A method for preparing a compound of formula K:

• wherein:
• A is an acid;
• and
• n is 1, 2 or 3;
• comprising the steps of
• (a) providing a compound of formula B
• wherein:
• R2 is a suitable amino protecting group;
• and
• R4 is a suitable amino protecting group;
• (b) sulfonating the compound of formula B to form a compound of formula F-2a:
• wherein:
• M is a metal selected from alkali metals;
• (c) condensing the compound of formula F-2a with compound F-1:
• or a salt thereof,
• to form a compound of formula Q:
• (d) reducing the compound of formula Q to form a compound of formula P:
• (e) reacting the compound of formula P with a compound of formula F-3:
• wherein:
• R3 is a suitable benzimidazole protecting group;
• and
• L is a suitable leaving group;
• to form a compound of formula O:
• (f) deprotecting the compound of formula to form a compound of formula N:
• (g) deprotecting the compound of formula N to form a compound of formula M:
• and
• (h) deprotecting the compound of formula M to form the compound of formula K.

A method for preparing a compound of formula P:

• wherein:
• R2 is a suitable amino protecting group;
• and
• R4 is a suitable amino protecting group;
• comprising the steps of:
• (a) providing a compound of formula B:
• (b) sulfonating the compound of formula B to form a compound of formula F-2a:
• wherein:
• M is a metal selected from alkali metals;
• (c) condensing the compound of formula F-2a with compound F-1:
• or a salt thereof;
• to form a compound of formula Q:
• and
• (d) reducing the compound of formula Q to form the compound of formula P.

A method for preparing a compound of formula F-2a:

• wherein:
• R2 is a suitable amino protecting group;
• R4 is a suitable amino protecting group;
• and
• M is a metal selected from alkali metals;
• comprising the steps of:
• (a) providing a compound of formula B:
• and
• (b) sulfonating the compound of formula B to form the compound of formula F-2a.

A compound of formula F-2:

• wherein:
• R1 is hydrogen, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —S(O)mR′, —Si(R′)3 or an optionally substituted group selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, phenyl, aryl, or heteroaryl;
• R2 and R4 independently are hydrogen, —C(O)R′, —C(O)OR′, —C(O)NR′R″, —S(O)mR′, —Si(R′)3 or an optionally substituted group selected from C1-C6 alkyl, C1—C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, phenyl, aryl, or heteroaryl;
• R′ and R″ independently are hydrogen or an optionally substituted group selected from C1-6 aliphatic, a 3-8 membered saturated or partially unsaturated monocyclic carbocyclic ring, phenyl, an 8-10 membered bicyclic aromatic carbocyclic ring, a 4-8 membered saturated or partially unsaturated monocyclic heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 5-6 membered monocyclic heteroaromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered bicyclic heteroaromatic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
• and
• M is a metal selected from alkali metals.

A compound of formula K:

• wherein:
• A is H2SO4;
• and
• n is 1, 2 or 3.