HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-(4-Dimethylaminobenzyl) 4-hydroxy-1-methyl-1H-indole-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-(aminomethyl)-N,N-dimethylaniline dihydrochloride | HCID 2734633 | — |
| Reactant | 4-Hydroxy-1-methyl-1H-indole-2-carboxylic acid | HCID 10219758 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-(4-Dimethylaminobenzyl) 4-hydroxy-1-methyl-1H-indole-2-carboxamide | HCID 9949122 | 69% |
Reaction Steps
To a solution of 4-hydroxy-1-methyl-1H-indole-2-carboxylic acid (Example 10, 0.12 g) in DMF (10 mL) was added TBTU (0.20 g), HOBt (0.10 g) and DIEA (0.35 mL). After 5 min., 4-(dimethylamino)benzylamine dihydrochloride (0.14 g) was added and stirring was continued overnight under nitrogen at room temperature. The residue remaining after DMF evaporation was purified by reversed phased chromatography on C18 silica with a trifluoroacetic acid (0.025%) acidified acetonitrile water gradient to give 0.14 g of the title compound. MS ES (M++H)=324.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07402604B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-b2a4616cb6cc48769db4756ea5140f64 |
| Source note | uspto-grants-2008_07 |