HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 178490989, compound
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 | 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine carboxylic acid | HCID 118157517 | — |
| Reactant | HCID 178511715 | HCID 178511715 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178490989 | HCID 178490989 | 30.4% |
Reaction Steps
In DMF (10 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine formic acid (0.8 g, 1.94 mmol). The solution was cooled in an ice bath. HATU (1.11 g, 2.91 mmol) and DIPEA (0.37 g, 2.87 mmol) were added. After 20 min, trans-4-aminocyclohexanol (0.27 g, 2.3 mmol) was added in batches. The reaction was conducted overnight. LC-MS was used to monitor the reaction. The reaction mixture was poured into water (50 mL) and filtrated. The solid was recrystallized with acetone (20 mL) to give N-((trans)-4-hydroxycyclohexan-1-yl)-4-((3-chloro-4-methoxybenzyl)amino)-2-(5H-pyrrolo[3,4-b]pyridin-6(7H)yl)-5-pyrimidine formamide (300 mg, 30.3% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359371B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-beff835950fb4d5eb9c049fdf614f80e |
| Source note | uspto-grants-2016_06 |