Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bromoacetic anhydride | HCID 4259817 | — |
| Reactant | HCID 178507700 | HCID 178507700 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 3010832 | HCID 3010832 | 56.2% |
Reaction Steps
Bromoacetic anhydride (290 mg) is added to a stirred solution of 8-amino-N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (Preparation 3, 426 mg) in anhydrous DMF (5.0 mL). After 30 min, triethylamine (100 mg) and additional bromoacetic anhydride (100 mg) are added. After 1 h, triethylamine (300 mg) is added and the solution is heated briefly at 80° C. Methanol (8 mL) is added and the resulting precipitate is filtered off, washed with water and dried to afford 262 mg of the title compound as a DMF solvate. Physical characteristics: 1H NMR (DMSO-d6) δ2.37, 2.73, 2.89, 3.53, 3.57, 4.56, 5.11, 7.23, 7.35, 7.40, 7.72, 7.95, 8.72, 10.35, 11.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06624159B2 |
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| Source dataset | uspto-grants-2003_09 |
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| ORD ID | ord-aec3249ff9d7437abf4958a8db5254f6 |
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| Source note | uspto-grants-2003_09 |
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