Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| 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 | HCID 67059669 | HCID 67059669 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 50991747 | HCID 50991747 | 54.6% |
Reaction Steps
A mixture of 3-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-1-methyl-1H-pyrazole-5-carboxylic acid (39.8 mg, 0.086 mmol), HATU (49.0 mg, 0.129 mmol) and dimethylamine, 2M in THF (0.086 mL, 0.172 mmol) in DMF (2 mL) was stirred at room temperature for 2 h. Water was added and the reaction mixture was extracted with ethyl acetate 3 times. The combined organic layers were washed twice with 10% lithium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude was purified by preparative HPLC to give N,N-dicyclopropyl-4-(5-(dimethylcarbamoyl)-1-methyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (23 mg, 54.1% yield) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08202881B2 |
|---|
| Source dataset | uspto-grants-2012_06 |
|---|
| ORD ID | ord-edbfc502f95746c1b7eeb02415f13c1c |
|---|
| Source note | uspto-grants-2012_06 |
|---|
