関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | 1,5-dimethyl-1H-pyrazol-3-amine | HCID 7017747 | — |
| 反応物 | 4-iodo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide | HCID 58180649 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | Bms-911543 | HCID 50922691 | 31.7% |
反応手順
To a vial containing 1,5-dimethyl-1H-pyrazol-3-amine (13.60 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 μmol), Xantphos (5.90 mg, 10.20 μmol), and cesium carbonate (100 mg, 0.306 mmol) was added N,N-dicyclopropyl-6-ethyl-4-iodo-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (45.8 mg, 0.102 mmol) in DME (1020 μL). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 90° C. 1 h. The reaction mixture was diluted with dichloromethane and vacuum filtered through Celite. The filtrate was concentrated in vacuo. The crude residue was purified via flash column chromatography using an ISCO 12 g column eluting with 1-10% MeOH/CH2Cl2). N,N-Dicyclopropyl-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (14 mg, 31.7% yield) was isolated as an off-white solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08202881B2 |
|---|
| 出典データセット | uspto-grants-2012_06 |
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| ORD ID | ord-dfea846404ed4fea81b7bc61544c16f1 |
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| 出典メモ | uspto-grants-2012_06 |
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