Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride | HCID 44541812 | — |
| Reactant | (4S)-6-Azaspiro[2.5]octan-4-ol | HCID 44541813 | — |
| Reactant | HCID 67074220 | HCID 67074220 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67087033 | HCID 67087033 | — |
Reaction Steps
A solution of 0.070 g (0.20 mmol) of 3-[(S)-4-(3,4-dichloro-phenylcarbamoyl)-3-methyl-2-oxo-piperazin-1-yl]-propionic acid (intermediate 12) in 1.5 ml of DMF was treated with 0.045 ml (0.28 mmol) of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2), 0.054 ml (0.40 mmol) of triethylamine and at 0° C. with 0.081 g (0.22 mmol) of HATU. Over night, the suspension was naturally warmed to RT, poured on aqueous 10% KHSO4 solution and extracted with EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after purification with flash chromatography (SiO2, dichloromethane/methanol 99:1 to 96:4) 0.069 g (70%) of the titled compound as white foam. MS: 483.2 (MH+, 2Cl).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445674B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-0435f287bad64e05b1c1470baafc652d |
|---|
| Source note | uspto-grants-2013_05 |
|---|
