Processes for the preparation of rivaroxaban and intermediates thereof
Provided are process for the preparation of (R)- and/or (S)-Rivaroxaban, and compounds which are intermediate compounds used in the processes for the preparation of (R)- and/or (S)-Rivaroxaban.
1. A compound of Formula 13:
wherein
G 1 is OR 1 , NR 2 R 3 or CQ 3 ;
R 1 is alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl or substituted arylalkyl;
R 2 and R 3 are either (a) two independent groups or (b) together form a single ring group with the N to which they are bonded;
R 2 and R 3 , when independent groups, are independently selected from the group consisting of: H, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl and substituted arylalkyl;
R 2 and R 3 , when together form a single ring group with the N to which they are bonded, are a heteroaryl ring;
Q is halogen; and
G 2 is a primary amine precursor.
2. The compound of claim 1 wherein G 1 is OR 1 and G 2 is an azide or NR 2 ′R 3 ′, wherein R 2 ′ and R 3 ′ are either two independent groups or together form a single ring group with the N to which they are bonded; R 2 ′ and R 3 ′, when independent groups, are independently selected from the group consisting of: hydrogen and a suitable amine protecting group, provided that both R 2 ′ and R 3 ′ are not both hydrogen; R 2 ′ and R 3 ′, when together, form a single ring group with the N to which they are bonded, are a heterocyclic ring, a substituted heterocyclic ring, phthalimide or saccharin.
3. The compound of claim 1 wherein G 1 is OR 1 and G 2 is an azide heterocyclic or substituted heterocyclic ring.
4. The compound of claim 3 wherein R 1 is an alkyl and G 2 is a heterocyclic ring or a substituted heterocyclic ring.
5. The compound of claim 4 wherein G 1 is methoxy and G 2 is phthalimide.