Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | Cyanoacetaldehyde | HCID 151404 | — |
| Reactant | 3-Pyridinecarboxylic acid, 4-(trifluoromethyl)- | HCID 2777549 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Catalyst | Mercury bis(trifluoroacetate) | HCID 2723924 | — |
| Solvent | Dimethyl sulfoxide methanol | HCID 22036561 | — |
| Product | HCID 58557214 | HCID 58557214 | 15% |
Reaction Steps
A mixture of 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (0.067 g, 0.18 mmol, prepared using O from 4-(trifluoromethyl)nicotinic acid, N, H with Example #5, Step C, HATU and DIEA, Q with Lawesson's reagent and mercury (II) trifluoroacetate, D with NaOH, F, H with 2-cyanoacetic acid, HATU, and DIEA) was dissolved in DMSO:MeOH (2:1, 3 mL). The mixture was separated using Varian 218 LC pumps, a Varian CVM 500 with switching valves and heaters for automatic solvent, column and temperature control and a Varian 701 Fraction collector using Method 4 (Table 2) to give 3-((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (Rt=12.2 min, or =positive) (0.0284 g, 15%) [AA.1.1] and 3-((3S,4S)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrde (Rt=5.3 min, or =negative) (0.0282 g, 15%) [AA.1.2]: LC/MS (Table 1, Method b) Rt=1.55 min; MS m/z: 377 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08426411B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-88c4f64b836243808284e5444abbe14b |
|---|
| Source note | uspto-grants-2013_04 |
|---|
