Table 6.
Reaction conditions for 1-Phenylcyclopropane carboxamide derivative (8a).
S.No | Reagent | Base | Solvent | Time (h) | Yield (%) |
---|---|---|---|---|---|
1 | EDC | Et3N | THF | 20 | 41 |
2 | EDC | Et3N | DMF | 18 | 45 |
3 | EDC | DIPEA | THF | 16 | 62 |
4 | EDC | DIPEA | DMF | 12 | 65 |
5 | HATU | Et3N | THF | 20 | 46 |
6 | HATU | Et3N | DMF | 18 | 49 |
7 | HATU | DIPEA | THF | 16 | 75 |
8 | HATU | DIPEA | DMF | 12 | 85 |
9 | HBTU | Et3N | THF | 20 | 48 |
10 | HBTU | Et3N | DMF | 18 | 51 |
11 | HBTU | DIPEA | THF | 16 | 68 |
12 | HBTU | DIPEA | DMF | 12 | 70 |
13 | T3P | Et3N | THF | 20 | 47 |
14 | T3P | Et3N | DMF | 18 | 49 |
15 | T3P | DIPEA | THF | 16 | 64 |
16 | T3P | DIPEA | DMF | 12 | 68 |
*All reactions were carried out on a 10 mg scale. The reaction was monitored by TLC and LCMS. Acid (1.0 eq), Amine (1.0 eq), coupling reagent (1.5 eq), base (3.0 eq), solvent (5 vol). EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide). HATU (1-[Bis(dimethylamino) methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluoro phosphate). HBTU (3-[Bis(dimethylamino)methyliumyl]-3H-benzotriazol-1-oxide hexafluorophosphate). T3P (Propanephosphonic acid anhydride).