HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 5-[5-(1H-Pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2774010 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 4-[8-(4-Morpholin-4-yl-phenylamino)imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-one | HCID 24857447 | — |
| Reactant | 5-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide | HCID 59023115 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | 5-[5-(1H-Pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide | HCID 59023114 | 18.3% |
Reaction Steps
In the same way as described for Compound 85, step 1, using 5-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide (169 mg, 0.39 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (91 mg, 0.47 mmol), Pd(PPh3)4 (45 mg, 0.039 mmol) and NaOtBu (150 mg, 1.56 mmol) in DMF:water (3:1, 9 mL). The crude residue is purified by reverse phase preparative HPLC to give the title compound (30 mg, 18%). LCMS: Rt 1.81 min (97.6%); m/z (APCI) 420 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 1.02 (6H, t), 2.36-2.71 (4H, m), 3.09-3.40 (4H, m), 7.73 (1H, s), 7.84 (1H, s), 8.04 (1H, d), 8.24 (3H, m), 8.56 (1H, m), 8.79 (1H, d), 9.28 (1H, s), 10.24 (1H, s), 13.40 (1H, br s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173656B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-e7db731ae5db4794bbc91d71d047eaae |
| Source note | uspto-grants-2012_05 |