Solid support reagents for synthesis
View Patent ↗The present invention relates to a compound according to the formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Y, Z, n, s, and t are as defined herein. These compounds are useful for methods of solid phase synthesis.
1. A compound according to Formula II:
wherein
R 1 is selected from hydrogen and C 1 -C 6 alkyl;
R 2 is selected from hydrogen, hydroxy, OC(O)CH 3 , C 1 -C 6 alkoxy, and C 1 -C 6 alkyl, or together R 1 and R 2 form a single bond;
R 7 and R 8 are each independently selected from hydroxy, halogen, hydrogen, C 1 -C 6 alkoxy, and OC(O)CH 3 , or together R 7 and R 8 form a carbonyl;
X 1 , X 3 , and X 4 are selected from hydrogen, halogen, nitro, and amino;
X 2 is selected from nitro, —NH 2 , alkylamino, and dialkylamino;
Y is methylene;
n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
Z is OR;
R is selected from hydrogen, SiR a R b R c , CR a R b R c , heteroalkyl, and C 1 -C 6 alkyl;
R a , R b , and R c are the same as or different from each other and each represents methyl, ethyl, i-propyl, t-butyl, phenyl or substituted phenyl.
2. The compound of claim 1 , wherein together R 7 and R 8 form a carbonyl.
3. The compound of claim 1 , wherein together R 1 and R 2 form a single bond.
4. The compound of claim 1 , wherein R 1 is hydrogen.
5. The compound of claim 1 , wherein one of R 7 or R 8 is OC(O)CH 3 and the other is hydrogen.
6. The compound of claim 1 , wherein one of R 7 or R 8 is hydroxy and the other is hydrogen.
7. The compound of claim 1 , wherein X 2 is nitro.
8. The compound of claim 1 , wherein n is 6.
9. The compound as in claim 1 , wherein R is selected from hydrogen, Si(t-butyl)(CH 3 ) 2 , and C(C 6 H 5 )(4-MeOC 6 H 4 ) 2 .
10. The compound of claim 1 , wherein at least one of X 1 , X 3 , and X 4 is halogen.
11. The compound of claim 1 , wherein R 1 and R 2 form a single bond; together R 7 and R 8 form a carbonyl; X 1 , X 3 , and X 4 are hydrogen; X 2 is —NH 2 ; Y is methylene;
n is 6; and Z is OR, wherein, R is CR a R b R c .
12. The compound, of claim 1 , having the structure:
13. The compound of claim 1 , wherein R 1 is hydrogen; R 2 is OC(O)CH 3 ; R 7 and R 8 are hydrogen; X 1 , X 3 , and X 4 are hydrogen; X 2 is NH 2 ; Y is methylene; and n is 6; Z is OR, wherein, R is CR a R b R c .
14. A compound having the following Formula IV:
wherein
is a solid support;
the wavy line represents a carbon chain which optionally contains a carbonyl;
W is selected from hydrogen and C 1 -C 6 alkyl;
R 1 is selected from hydrogen and C 1 -C 6 alkyl;
R 2 is selected from hydrogen, hydroxy, OC(O)CH 3 , C 1 -C 6 alkoxy, and C 1 -C 6 alkyl, or together R 1 and R 2 form a single bond;
R 7 and R 8 are each independently selected from hydroxy, halogen, hydrogen, C 1 -C 6 alkoxy, and OC(O)CH 3 , or together R 7 and R 8 form a carbonyl;
X 1 , X 3 and X 4 are selected from hydrogen, halogen, nitro, and amino;
Y is methylene; and
n is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10;
Z is OR;
R is selected from hydrogen, SiR a R b R c , CR a R b R c , heteroaryl, and C 1 -C 6 alkyl;
R a , R b , and R c are the same as or different from each other and each represents methyl, ethyl, i-propyl, t-butyl, phenyl or substituted phenyl.
15. The compound of claim 14 , wherein the solid support is selected from controlled pore glass (CPG), styrene-divinylbenzene (DVB) co-polymer, polyethylene glycol (PEG) and methacrylate based polymer.
16. The compound of claim 14 , wherein the carbon chain is a carbonyl.
17. The compound of claim 16 , wherein R 1 and R 2 form a single bond; R 7 and R 8 form a carbonyl; X 1 , X 3 , and X 4 are hydrogen; W is a hydrogen; Y is methylene; n is 6; and Z is OR, wherein, R is CR a R b R c .
18. The compound of claim 16 , wherein R 1 is hydrogen; R 2 is an OC(O)CH 3 ; R 7 and R 8 are hydrogen; X 1 , X 3 , and X 4 are hydrogen; W is a hydrogen; Y is methylene; n is 6; and Z is OR, wherein, R is CR a R b R c .
19. The compound of claim 14 , having the structure: