HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 4-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid | HCID 67994996 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate | HCID 67994849 | 88.2% |
Reaction Steps
A solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.1408 g, 0.262 mmol), ammonium chloride (0.056 g, 1.050 mmol), BOP (0.151 g, 0.341 mmol), DIPEA (0.220 mL, 1.260 mmol) and N-methylmorpholine (0.113 mL, 1.023 mmol) in DMF (2.187 mL) was stirred for 1 hr. Water (22 mL) was added, and the precipitate was filtered, washed with water, dried over Drierite to give the desired product (0.1277 g, 0.231 mmol, 88% yield) as a light tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08685969B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-4514f36ef0f44d24a98845d2cce12acf |
| Source note | uspto-grants-2014_04 |