Patent ID: 6835841
Filing Date: 2004-12-28
Classification: C07D

Abstract:
A process of forming a compound of formula II, comprising: (a) contacting a compound of formula I with sub-stoichiometric amounts of a platinum catalyst in the presence of a solvent under hydrogen pressure and super-stoichiometric amounts of an acid; wherein: the platinum catalyst is platinum on charcoal (Pt/C) or Adam's catalyst (platinum(IV)-dioxide, PtO2); the solvent is a protic solvent or a mixture of protic and aprotic solvents; ring B is a 4-7 membered non-aromatic carbocyclic or heterocyclic ring consisting of: carbon atoms, 0-3 carbonyl groups, 0-3 double bonds, and 0-2 ring heteroatoms selected from O, N, NR6, and S(O)p, provided that ring B contains other than a Sâ€”S, Oâ€”O, or Sâ€”O bond; R1 is Q, â€”C1-6 alkylene-Q, â€”C2-6 alkenylene-Q, or â€”C2-6 alkynylene-Q; R2 is Q, â€”C1-6 alkylene-Q, â€”C2-6 alkenylene-Q, â€”C2-6 alkynylene-Q, â€”(CRaRa1)rO(CRaRa1)s-Q, â€”(CRaRa1)rNRa(CRaRa1)s-Q, â€”(CRaRa1)rC(O)(CRaRa1)s-Q, â€”(CRaRa1)rC(O)O(CRaRa1)s-Q, â€”(CRaRa1)rC(O)NRaRa1, â€”(CRaRa1)rC(O)NRa(CRaRa1)s-Q, â€”(CRaRa1)rS(O)p(CRaRa1)s-Q, or â€”(CRaRa1)rSO2NRa(CRaRa1)s-Q; Q is, independently at each occurrence, H, a C3-6 carbocycle substituted with 0-3 Rd, or a 5-10 membered heterocycle consisting of: carbon atoms and 1-4 heteroatoms selected from the group consisting of N, O, and S(O)p, and substituted with 0-3 Rd; R3 is H, Cl, F, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, â€”(CH)r-phenyl substituted with 0-3 Rd, or â€”(CH)r-5-6 membered heterocycle consisting of: carbon atoms and 1-4 heteroatoms selected from the group consisting of N, O, and S(O)p, and substituted with 0-3 Rd; alternatively, when R2 and R3 are attached to the same carbon atom, they form a 3-8 membered carbocyclic or heterocyclic spiro ring C substituted with 0-2 Rc and consisting of carbon atoms, 0-4 heteroatoms selected from O, N, and S(O)p, and 0-2 double bonds, provided that ring C contains other than a Sâ€”S, Oâ€”O, or Sâ€”O bond; alternatively, when R2 and R3 are attached to adjacent carbon atoms, together with the carbon atoms to which they are attached they form a 5-7 membered carbocyclic or heterocyclic ring D substituted with 0-2 Rc and consisting of carbon atoms, 0-2 heteroatoms selected from the group consisting of N, O, and S(O)p, and 0-3 double bonds; R4 is H, C1-6 alkyl substituted with 0-1 Rb, C2-6 alkenyl substituted with 0-1 Rb, or C2-6 alkynyl substituted with 0-1 Rb; R5 is â€”CH2ORa or â€”C(O)ORa; R6 is Q, â€”C1-6 alkylene-Q, â€”C2-6 alkenylene-Q, â€”C2-6 alkynylene-Q, â€”(CRaRa1)rC(O)(CRaRa1)s-Q, â€”(CRaRa1)rC(O)â€”C2-6 alkenylene-Q, â€”(CRaRa1)rC(O)O(CRaRa1)s-Q, â€”(CRaRa1)rC(O)NRaRa1, â€”(CRaRa1)rC(O)NRa(CRaRa1)s-Q, â€”(CRaRa1)rS(O)p(CRaRa1)s-Q, or â€”(CRaRa1)rSO2NRa(CRaRa1)s-Q; Ra is, independently at each occurrence, H, C1-6 alkyl, phenyl, or benzyl; Ra1 is, independently at each occurrence, H or C1-6 alkyl; Ra2 is, independently at each occurrence, C1-6 alkyl, phenyl, or benzyl; Rb is, independently at each occurrence, C1-6 alkyl substituted with 0-1 Rc, â€”ORa, â€”SRa, Cl, F, Br, I, &boxH;O, CN, NO2, â€”NRaRa1, â€”C(O)Ra, â€”C(O)ORa, â€”C(O)NRaRa1, â€”C(S)NRaRa1, â€”NRaC(O)NRaRa1, â€”OC(O)NRaRa1, â€”NRaC(O)ORa, â€”S(O)2NRaRa1, â€”NRaS(O)2Ra2, â€”NRaS(O)2NRaRa1, â€”OS(O)2NRaRa1, â€”S(O)pRa2, CF3, â€”CF2CF3, â€”CHF2, â€”CH2F, or phenyl; Rc is, independently at each occurrence, H, C1-4 alkyl, â€”ORa, Cl, F, Br, I, &boxH;O, CF3, CN, NO2, â€”C(O)Ra, â€”C(O)ORa, â€”C(O)NRaRa, or â€”S(O)pRa; Rd is, independently at each occurrence, C1-6 alkyl, â€”ORa, Cl, F, Br, I, &boxH;O, CN, NO2, â€”NRaRa1, â€”C(O)Ra, â€”C(O)ORa, â€”C(O)NRaRa1, â€”C(S)NRaRa1, â€”NRaC(O)NRaRa1, â€”OC(O)NRaRa1, â€”NRaC(O)ORa, â€”S(O)2NRaRa1, â€”NRaS(O)2Ra2, â€”NRaS(O)2NRaRa1, â€”OS(O)2NRaRa1, â€”S(O)pRa2, CF3, â€”CF2CF3, C3-10 carbocycle, or a 5-6 membered heterocycle consisting of: carbon atoms and 1-4 heteroatoms selected from the group consisting of N, O, and S(O)p; p, at each occurrence, is selected from 0, 1, and 2; r, at each occurrence, is selected from 0, 1, 2, 3, and 4; and s, at each occurrence, is selected from 0, 1, 2, 3, and 4.