Table 3.

Proof library: Coupling reactions to generate a library of 9-aminoacridines (10)

Entry	9-chloroacridine	Diamine component	Product	Yield (purity)a
1	7{1,1}	9{1,9}	10{1,1,1,9} · 2HCl	52% (100%)
2	7{1,2}	9{1,9}	10{1,2,1,9} · 2HCl	16% (83%)
3	7{1,3}	9{1,9}	10{1,3,1,9} · 2HCl	Failed
4	7{1,4}	9{1,9}	10{1,4,1,9} · 2HCl	19% (100%)
5	7{2,1}	9{1,9}	10{2,1,1,9} · 2HCl	22% (95%)
6	7{2,2}	9{1,9}	10{2,2,1,9} · 2HCl	4% (81%)
7	7{2,3}	9{1,9}	10{2,3,1,9} · 2HCl	Failed
8	7{2,4}	9{1,9}	10{2,4,1,9} · 2HCl	21% (92%)
9	7{3,1}	9{1,9}	10 {3,1,1,9} · 2HCl	8% (56%)
10	7{3,2}	9{1,9}	10{3,2,1,9} · 2HCl	15% (50%)
11	7{3,3}	9{1,9}	10{3,3,1,9} · 2HCl	Failed
12	7{4,1}	9{1,9}	10{4,1,1,9} · 2HCl	22% (81%)
13	7{4,2}	9{1,9}	10{4,2,1,9} · 2HCl	22% (73%)
14	7{4,4}	9{1,9}	10{4,4,1,9} · 2HCl	Failed
15	7{1,5}	9{1,9}	10{1,5,1,9} · 2HCl	10% (73%)
16	7{4,6}	9{1,1} · 2TFA	10{4,6,1,1} · 2HCl	32% (81%)
17	7{4,6}	9{1,2} · 2TFA	10{4,6,1,2} · 2HCl	18% (100%)
18	7{4,6}	9{1,3}	10{4,6,1,3} · 2HCl	48% (100%)
19	7{4,6}	9{1,4}	10{4,6,1,4} · 2HCl	34% (100%)
20	7{4,6}	9{1,5}	10{4,6,1,5} · 2HCl	52% (100%)
21	7{4,6}	9{1,6}	10{4,6,1,6} · 2HCl	32% (95%)
22	7{4,6}	9{1,7}	10{4,6,1,7} · 2HCl	Failed
23	7{4,6}	9{1,8}	10{4,6,1,8} · 2HCl	19% (68%)
24	7{4,6}	9{2,1} · 2TFA	10{4,6,2,1} · 2HCl	34% (100%)
25	7{4,6}	9{2,2} · 2TFA	10{4,6,2,2} · 2HCl	60% (100%)
26	7{4,6}	9{2,3}	10{4,6,2,3} · 2HCl	69% (100%)
27	7{4,6}	9{2,4}	10{4,6,2,4} · 2HCl	62% (100%)
28	7{4,6}	9{2,5}	10{4,6,2,5} · 2HCl	73% (100%)
29	7{4,6}	9{2,6}	10{4,6,2,6} · 2HCl	47% (90%)
30	7{4,6}	9{2,7}	10{4,6,2,7} · 2HCl	Failed
31	7{4,6}	9{2,8}	10{4,6,2,8} · 2HCl	51% (87%)

^aPurity determined by RP-HPLC-MS integration detected at 254 nm.