HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-[(2,2-Difluorocyclopropyl)methyl]-5-[2-(isoxazol-3-ylcarbonyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | 3-Isoxazolecarboxylic acid | HCID 11286453 | — |
| Reactant | 1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclopenta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 71135227 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-[(2,2-Difluorocyclopropyl)methyl]-5-[2-(isoxazol-3-ylcarbonyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 71135228 | — |
Reaction Steps
1-[(2,2-Difluorocyclopropypmethyl]-5-(1,2,3,3a,4,6a-hexahydrocyclopenta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (14-2, 50 mg, 0.14 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 24.4 mg, 0.21 mmol, 1.5 equiv), DIPEA (0.076 mL, 0.43 mmol, 3.0 equiv) and HATU (82 mg, 0.21 mmol, 1.5 equiv) were added to anhydrous acetonitrile (3 mL). After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O) provided 14-3 as a white solid. MS m/z (M+H): calculated=442.1688; observed=442.1703.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09315518B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-343ac5cd4de844f5aa94e5d6481bf657 |
| Source note | uspto-grants-2016_04 |