HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium t-butoxide → 5-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide | HCID 24857547 | — |
| Reactant | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| Reactant | 5-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide | HCID 59023116 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Ammonia | HCID 222 | — |
| Product | 5-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide | HCID 59023115 | 72% |
Reaction Steps
In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (0.272 g, 0.982 mmol), 5-amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide (0.197 g, 0.835 mmol), NaOtBu (0.132 g, 1.37 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), Xantphos (22 mg, 0.038 mmol) and toluene (3 mL). The crude material is purified by silica gel column chromatography eluting with DCM followed by 94:6 DCM:NH3 (7M in MeOH) to afford the title compound (0.263 g, 72%). HPLC (254 nm) Rt 2.09 min (72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178530B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-5343a0bbbb864e9e8a1c748c65551114 |
| Source note | uspto-grants-2012_05 |