HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Pyridinemethanamine → 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Pyridinemethanamine | HCID 31018 | — |
| 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 | N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide | HCID 24857547 | — |
| Reactant | 4-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino) benzoic acid | HCID 58228829 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl benzamide | HCID 86616745 | — |
Reaction Steps
In the same way as described for Compound 90, step 3, using 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)benzoic acid (365 mg, 1.57 mmol), 3-aminomethylpyridine (0.16 mL, 1.57 mmol), N,N-diisopropylethylamine (0.42 mL, 2.35 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (715 mg, 1.9 mmol) and DMF (6 mL). The crude residue is purified using column chromatography, eluting with EtOAc followed by EtOAc:MeOH (95:5) then EtOAc:NH3 (7M in MeOH). The title amide is isolated as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173656B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-5c85de4d363f4be2977f8843145ebd49 |
| Source note | uspto-grants-2012_05 |