HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-(3-(2-oxopropyl)benzoyl)piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | 3-(2-Oxopropyl)benzoic acid | HCID 12254105 | — |
| Reactant | 4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide | HCID 66988311 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | 4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-(3-(2-oxopropyl)benzoyl)piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide | HCID 66988045 | 64% |
Reaction Steps
HATU (82 mg, 0.217 mmol), DIEA (0.103 mL, 0.59 mmol), and 3-(2-oxopropyl)benzoic acid (39 mg, 0.217 mmol) were added to a stirring solution of Intermediate 96 (110 mg, 0.197 mmol) in DMF (2 mL) at rt. The reaction mixture was stirred for 40 min then pour into H2O (50 mL). The resulting precipitate was filtered, washed with H2O, and dried to give crude di-amide (256 mg). Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (85 mg, 64%) as a yellow solid. ES/MS calcd. for C39H38N5O7S+ 720.3. Found m/z=720.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394829B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-fdb2b8154e52486e950845ae21b1fd0f |
| Source note | uspto-grants-2013_03 |