Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Guanidine Hydrochloride | HCID 5742 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | HCID 16090340 | HCID 16090340 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69063894 | HCID 69063894 | — |
Reaction Steps
To a solution of (2,5-diphenyl-pyrrol-1-yl)-acetic acid (1 eq.) in DMF is added CDI (1.2 eq.) and the mixture stirred at RT for 1 hour. Then add a solution of guanidine HCl (3 eq.) and triethylamine (3 eq.) in DMF is added. The reaction is stirred for 5 hours, then water is added and the mixture extracted with EtOAc, dried over MgSO4 and concentrated. The residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system. See Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 μM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07488832B2 |
|---|
| Source dataset | uspto-grants-2009_02 |
|---|
| ORD ID | ord-4b30e4bcc2a2471f90cd4a9ea4ba6176 |
|---|
| Source note | uspto-grants-2009_02 |
|---|